Term IRI Term label Parent term IRI Parent term label Alternative term Definition http://purl.obolibrary.org/obo/MOP_0000826 dienophilicity http://purl.obolibrary.org/obo/BFO_0000016 disposition A disposition which is realised in a [4+2] reaction with a double-bonded system. http://purl.obolibrary.org/obo/RXNO_0000621 Hell-Volhard-Zelinsky reaction http://purl.obolibrary.org/obo/MOP_0000550 halogenation An alpha-halogenation reaction where a carboxylic acid reacts with dibromine to form an alpha-bromocarboxylic acid. http://purl.obolibrary.org/obo/RXNO_0000622 Meerwein-Ponndorf-Verley reduction of an aldehyde http://purl.obolibrary.org/obo/RXNO_0000089 Meerwein-Ponndorf-Verley reduction Meerwein-Ponndorf-Verley reduction of an aldehyde to the corresponding primary alcohol. http://purl.obolibrary.org/obo/RXNO_0000623 Meerwein-Ponndorf-Verley reduction of a ketone http://purl.obolibrary.org/obo/RXNO_0000089 Meerwein-Ponndorf-Verley reduction Meerwein-Ponndorf-Verley reduction of a ketone to the corresponding secondary alcohol. http://purl.obolibrary.org/obo/RXNO_0000624 Heck-type reaction http://purl.obolibrary.org/obo/RXNO_0000002 carbon-carbon coupling reaction A carbon-carbon coupling reaction where an organohalide or triflate couples to a terminal olefin to produce an internal olefin. http://purl.obolibrary.org/obo/RXNO_0000626 chloro Heck reaction http://purl.obolibrary.org/obo/RXNO_0000024 Heck reaction A Heck reaction where an organochloride couples to a terminal olefin to produce an internal olefin, catalysed by palladium. http://purl.obolibrary.org/obo/RXNO_0000627 iodo Heck reaction http://purl.obolibrary.org/obo/RXNO_0000024 Heck reaction A Heck reaction where an organoiodide couples to a terminal olefin to produce an internal olefin, catalysed by palladium. http://purl.obolibrary.org/obo/RXNO_0000628 triflyloxy Heck reaction http://purl.obolibrary.org/obo/RXNO_0000024 Heck reaction A Heck reaction where an organotriflate couples to a terminal olefin to produce an internal olefin, catalysed by palladium. http://purl.obolibrary.org/obo/RXNO_0000629 bromo Heck-type reaction http://purl.obolibrary.org/obo/RXNO_0000624 Heck-type reaction A Heck-type reaction where an organobromide couples to a terminal olefin to produce an internal olefin. http://purl.obolibrary.org/obo/RXNO_0000630 chloro Heck-type reaction http://purl.obolibrary.org/obo/RXNO_0000624 Heck-type reaction A Heck-type reaction where an organochloride couples to a terminal olefin to produce an internal olefin. http://purl.obolibrary.org/obo/RXNO_0000631 acyclic Beckmann rearrangement http://purl.obolibrary.org/obo/RXNO_0000026 Beckmann rearrangement A Beckmann rearrangement where an acyclic amide is formed. http://purl.obolibrary.org/obo/RXNO_0000632 Baeyer–Emmerling indole synthesis http://purl.obolibrary.org/obo/RXNO_0000395 indole synthesis An indole synthesis where an ortho-nitrocinnamic acid reacts with iron powder in a basic solution to form an indole. http://purl.obolibrary.org/obo/RXNO_0000633 bromo Sonogashira coupling http://purl.obolibrary.org/obo/RXNO_0000137 Sonogashira coupling A Sonogashira coupling where the aryl halide is an aryl bromide. http://purl.obolibrary.org/obo/RXNO_0000634 bromo Suzuki coupling http://purl.obolibrary.org/obo/RXNO_0000140 Suzuki-Miyaura coupling A Suzuki coupling where the halide is a bromide. http://purl.obolibrary.org/obo/RXNO_0000635 bromo Suzuki-type coupling http://purl.obolibrary.org/obo/RXNO_0000592 Suzuki-type coupling A Suzuki-type coupling where the halide is a bromide. http://purl.obolibrary.org/obo/RXNO_0000636 bromolactonization http://purl.obolibrary.org/obo/RXNO_0000593 halolactonization A halolactionization where the halide is a bromide. http://purl.obolibrary.org/obo/RXNO_0000637 chloro Sonogashira coupling http://purl.obolibrary.org/obo/RXNO_0000137 Sonogashira coupling A Sonogashira coupling where the aryl halide is an aryl chloride. http://purl.obolibrary.org/obo/RXNO_0000638 chloro Suzuki coupling http://purl.obolibrary.org/obo/RXNO_0000140 Suzuki-Miyaura coupling A Suzuki coupling where the halide is a chloride. http://purl.obolibrary.org/obo/RXNO_0000639 chloro Suzuki-type coupling http://purl.obolibrary.org/obo/RXNO_0000592 Suzuki-type coupling A Suzuki-type coupling where the halide is a chloride. http://purl.obolibrary.org/obo/RXNO_0000640 chlorolactonization http://purl.obolibrary.org/obo/RXNO_0000593 halolactonization A halolactionization where the halide is a chloride. http://purl.obolibrary.org/obo/RXNO_0000641 Conrad-Limpach cyclisation http://purl.obolibrary.org/obo/MOP_0000825 dealcoholative condensation Reaction of an arylamine wtih a beta-ketoester to yield a 4-hydroxyquinoline. http://purl.obolibrary.org/obo/RXNO_0000642 Combes quinoline synthesis http://purl.obolibrary.org/obo/MOP_0000628 molecular dehydration reaction Reaction of a beta-diketone with a primary arylamine to yield a quinoline. It is acid-catalysed. http://purl.obolibrary.org/obo/RXNO_0000655 Favorskii reaction http://purl.obolibrary.org/obo/RXNO_0000002 carbon-carbon coupling reaction A reaction between an alkyne and a carbonyl group under basic conditions in which a terminal alkyne serves as the CH-acidic moiety. When the carbonyl is an aldehyde, the 'Favorskii rearrangement' (RXNO:0000385) takes place and leads to an enone. http://purl.obolibrary.org/obo/CHEBI_27024 toluenes http://purl.obolibrary.org/obo/CHEBI_22712 benzenes Any member of the class of benzenes that is a substituted benzene in which the substituents include one (and only one) methyl group. http://purl.obolibrary.org/obo/CHEBI_29256 thiol http://purl.obolibrary.org/obo/CHEBI_23367 molecular entity An organosulfur compound in which a thiol group, -SH, is attached to a carbon atom of any aliphatic or aromatic moiety. http://purl.obolibrary.org/obo/CHEBI_38101 organonitrogen heterocyclic compound http://purl.obolibrary.org/obo/CHEBI_35352 organonitrogen compound Any organonitrogen compound containing a cyclic component with nitrogen and at least one other element as ring member atoms. http://purl.obolibrary.org/obo/CHEBI_51614 diarylmethane http://purl.obolibrary.org/obo/CHEBI_33659 organic aromatic compound Any compound containing two aryl groups connected by a single C atom. http://purl.obolibrary.org/obo/CHEBI_51867 methyl ketone http://purl.obolibrary.org/obo/CHEBI_17087 ketone A ketone of formula RC(=O)CH3 (R =/= H). http://purl.obolibrary.org/obo/CHEBI_15882 phenol http://purl.obolibrary.org/obo/CHEBI_33853 phenols An organic hydroxy compound that consists of benzene bearing a single hydroxy substituent. The parent of the class of phenols. http://purl.obolibrary.org/obo/CHEBI_17245 carbon monoxide http://purl.obolibrary.org/obo/CHEBI_23014 carbon oxide A one-carbon compound in which the carbon is joined only to a single oxygen. It is a colourless, odourless, tasteless, toxic gas. http://purl.obolibrary.org/obo/CHEBI_18310 alkane http://purl.obolibrary.org/obo/CHEBI_23367 molecular entity An acyclic branched or unbranched hydrocarbon having the general formula CnH2n+2, and therefore consisting entirely of hydrogen atoms and saturated carbon atoms. http://purl.obolibrary.org/obo/CHEBI_37963 pyranone http://purl.obolibrary.org/obo/CHEBI_26407 pyrans Any of a class of cyclic chemical compounds that contain an unsaturated six-membered ring with one ring oxygen atom and an oxo substituent. http://purl.obolibrary.org/obo/CHEBI_47985 enol ether http://purl.obolibrary.org/obo/CHEBI_25698 ether Ethers ROR' where R has a double bond adjacent to the oxygen of the ether linkage. http://purl.obolibrary.org/obo/CHEBI_59769 acetal http://purl.obolibrary.org/obo/CHEBI_36963 organooxygen compound An organooxygen compound having the structure RR'C(OR'')(OR''') (R'', R''' =/= H). Mixed acetals have R'' and R''' groups which differ. http://purl.obolibrary.org/obo/CHEBI_60004 mixture http://purl.obolibrary.org/obo/CHEBI_59999 chemical substance A mixture is a chemical substance composed of multiple molecules, at least two of which are of a different kind. http://purl.obolibrary.org/obo/CHEBI_22339 alkyne http://purl.obolibrary.org/obo/CHEBI_23367 molecular entity Acyclic branched or unbranched hydrocarbons having a carbon-carbon triple bond and the general formula CnH2n-2, RC#CR. http://purl.obolibrary.org/obo/CHEBI_24472 halohydrocarbon http://purl.obolibrary.org/obo/CHEBI_17792 organohalogen compound A compound derived from a hydrocarbon by replacing a hydrogen atom with a halogen atom. http://purl.obolibrary.org/obo/CHEBI_25566 nitrotoluene http://purl.obolibrary.org/obo/CHEBI_27024 toluenes Any member of the class of toluenes bearing one or more nitro substituents on the benzene ring. http://purl.obolibrary.org/obo/CHEBI_25707 organometallic compound http://purl.obolibrary.org/obo/CHEBI_23367 molecular entity A compound having bonds between one or more metal atoms and one or more carbon atoms of an organyl group. http://purl.obolibrary.org/obo/CHEBI_25713 organosilicon compound http://purl.obolibrary.org/obo/CHEBI_23367 molecular entity An organosilicon compound is a compound containing at least one carbon-silicon bond. http://purl.obolibrary.org/obo/CHEBI_2634 amidine http://purl.obolibrary.org/obo/CHEBI_23367 molecular entity Derivatives of oxoacids RnE(=O)OH in which the hydroxy group is replaced by an amino group and the oxo group is replaced by =NR. In organic chemistry an unspecified amidine is commonly a carboxamidine. http://purl.obolibrary.org/obo/CHEBI_26519 radical http://purl.obolibrary.org/obo/CHEBI_23367 molecular entity A molecular entity possessing an unpaired electron. http://purl.obolibrary.org/obo/CHEBI_33259 elemental molecular entity http://purl.obolibrary.org/obo/CHEBI_23367 molecular entity A molecular entity all atoms of which have the same atomic number. http://purl.obolibrary.org/obo/CHEBI_33598 carbocyclic compound http://purl.obolibrary.org/obo/CHEBI_33597 homocyclic compound A homocyclic compound in which all of the ring members are carbon atoms. http://purl.obolibrary.org/obo/CHEBI_60983 alkylphosphonate http://purl.obolibrary.org/obo/CHEBI_37592 organic phosphonate An organic phosphonate containing a C-PO(OH)2 or C-PO(OR)2 group (where R = alkyl group). http://purl.obolibrary.org/obo/CHEBI_68452 azole http://purl.obolibrary.org/obo/CHEBI_38101 organonitrogen heterocyclic compound Any monocyclic heteroarene consisting of a five-membered ring containing nitrogen. Azoles can also contain one or more other non-carbon atoms, such as nitrogen, sulfur or oxygen. http://purl.obolibrary.org/obo/CHEBI_5653 hemiacetal http://purl.obolibrary.org/obo/CHEBI_30879 alcohol A compound having the general formula RR'C(OH)OR'' (R'' =/= H). http://purl.obolibrary.org/obo/CHEBI_50978 boronate http://purl.obolibrary.org/obo/CHEBI_23367 molecular entity A salt or ester of boronic acid. http://purl.obolibrary.org/obo/CHEBI_61111 aminophosphonate http://purl.obolibrary.org/obo/CHEBI_35352 organonitrogen compound An organic phosphonate of formula (RO)2P(=O)-CR2-NR2; R can be H. http://purl.obolibrary.org/obo/MOP_0000825 dealcoholative condensation http://purl.obolibrary.org/obo/MOP_0000627 condensation reaction A reaction in which two or more reactants or remote reactive sites within the same molecular entity yield a single main product with accompanying formation of an alcohol molecule. http://purl.obolibrary.org/obo/RXNO_0000574 cyclic Beckmann rearrangement http://purl.obolibrary.org/obo/RXNO_0000347 azacycle synthesis A Beckmann rearrangement which produces a cyclic product. http://purl.obolibrary.org/obo/RXNO_0000575 Dess-Martin aldehyde oxidation http://purl.obolibrary.org/obo/RXNO_0000256 Dess-Martin oxidation A Dess-Martin oxidation of a primary alcohol to an aldehyde. http://purl.obolibrary.org/obo/RXNO_0000576 Dess-Martin ketone oxidation http://purl.obolibrary.org/obo/RXNO_0000256 Dess-Martin oxidation A Dess-Martin oxidation of a secondary alcohol to a ketone. http://purl.obolibrary.org/obo/RXNO_0000577 Friedlander quinoline synthesis http://purl.obolibrary.org/obo/RXNO_0000393 quinoline synthesis Synthesis of a quinoline by reaction of a 2-aminobenzaldehyde with a ketone. http://purl.obolibrary.org/obo/RXNO_0000578 Gewald reaction http://purl.obolibrary.org/obo/RXNO_0000348 thiacycle synthesis Reaction of an aldehyde or ketone with an alpha-cyanoester to form a 2-aminothiophene. http://purl.obolibrary.org/obo/RXNO_0000579 iodo Sonogashira coupling http://purl.obolibrary.org/obo/RXNO_0000137 Sonogashira coupling A Sonogashira coupling where the aryl halide is an aryl iodide. http://purl.obolibrary.org/obo/RXNO_0000580 iodo Suzuki coupling http://purl.obolibrary.org/obo/RXNO_0000140 Suzuki-Miyaura coupling A Suzuki coupling where the halide is an iodide. http://purl.obolibrary.org/obo/RXNO_0000581 iodo Suzuki-type coupling http://purl.obolibrary.org/obo/RXNO_0000592 Suzuki-type coupling A Suzuki-type coupling where the halide is an iodide. http://purl.obolibrary.org/obo/RXNO_0000582 iodolactonization http://purl.obolibrary.org/obo/RXNO_0000593 halolactonization A halolactionization where the halide is an iodide. http://purl.obolibrary.org/obo/RXNO_0000583 Niementowski quinazoline synthesis http://purl.obolibrary.org/obo/RXNO_0000347 azacycle synthesis An azacycle synthesis where the product is a 4-oxo-3,4-dihydroquinazoline and the reactants are a 2-aminobenzoic acid and an amide. http://purl.obolibrary.org/obo/RXNO_0000584 Niementowski quinoline synthesis http://purl.obolibrary.org/obo/RXNO_0000393 quinoline synthesis A quinoline synthesis where the product is a gamma-hydroxyquinoline and the reactants are a 2-aminobenzoic acid and an aldehyde or ketone. http://purl.obolibrary.org/obo/RXNO_0000585 Pomeranz–Fritsch reaction http://purl.obolibrary.org/obo/RXNO_0000347 azacycle synthesis An azacycle synthesis where the product is an isoquinoline and the reactants are a benzaldehyde and a 2,2-dialkoxyethylamine. http://purl.obolibrary.org/obo/RXNO_0000586 Steglich esterification http://purl.obolibrary.org/obo/RXNO_0000360 O-acylation to ester An O-acylation to ester where dicyclohexylcarbodiimide is used as a coupling reagent and 4-dimethylaminopyridine as a catalyst. http://purl.obolibrary.org/obo/RXNO_0000587 triflyloxy Sonogashira coupling http://purl.obolibrary.org/obo/RXNO_0000137 Sonogashira coupling A Sonogashira coupling where the role of the halide is played by a triflyloxy group. http://purl.obolibrary.org/obo/RXNO_0000588 triflyloxy Suzuki coupling http://purl.obolibrary.org/obo/RXNO_0000140 Suzuki-Miyaura coupling A Suzuki coupling where the rule of the halide is played by a triflyloxy group. http://purl.obolibrary.org/obo/RXNO_0000589 triflyloxy Suzuki-type coupling http://purl.obolibrary.org/obo/RXNO_0000592 Suzuki-type coupling A Suzuki-type coupling where the rule of the halide is played by a triflyloxy group. http://purl.obolibrary.org/obo/RXNO_0000590 Wenker synthesis http://purl.obolibrary.org/obo/MOP_0000628 molecular dehydration reaction Synthesis of an aziridine by dehydrating a beta aminoalcohol with sulfuric acid. http://purl.obolibrary.org/obo/RXNO_0000591 Hinsberg thiophene synthesis http://purl.obolibrary.org/obo/RXNO_0000348 thiacycle synthesis Reaction of an alpha-diketone with a dialkyl thiodiacetate to form a thiophene dicarboxylic acid. http://purl.obolibrary.org/obo/RXNO_0000592 Suzuki-type coupling http://purl.obolibrary.org/obo/RXNO_0000002 carbon-carbon coupling reaction The coupling of a boronic acid or boronic ester with an unsaturated halide, triflate or sulfonate. http://purl.obolibrary.org/obo/RXNO_0000593 halolactonization http://purl.obolibrary.org/obo/RXNO_0000346 oxacycle synthesis Addition of a carboxylic acid oxygen and halogen across a carbon-carbon double bond to form a lactone. http://purl.obolibrary.org/obo/RXNO_0000594 Ciamician-Dennstedt rearrangement http://purl.obolibrary.org/obo/RXNO_0000108 ring expansion Expansion of a pyrrole ring by heating with a halogeno compond to form a 3-halogenopyridine. http://purl.obolibrary.org/obo/RXNO_0000595 Claisen-Schmidt condensation http://purl.obolibrary.org/obo/MOP_0000628 molecular dehydration reaction Condensation of an aromatic aldehyde with an aliphatic aldehyde or ketone in the presence of a relatively strong base to from an alpha,beta-unsaturated aldehyde or ketone. http://purl.obolibrary.org/obo/RXNO_0000597 Corey-Bakshi-Shibata reduction http://purl.obolibrary.org/obo/MOP_0000580 ketone reduction Enantioselective reduction of a ketone to an alcohol with a chiral oxazaborolidine. http://purl.obolibrary.org/obo/RXNO_0000598 Johnson-Corey-Chaykovsky reaction http://purl.obolibrary.org/obo/RXNO_0000005 ring formation reaction step Reaction of a sulfur ylide with a double-bond to produce a three-membered ring. http://purl.obolibrary.org/obo/RXNO_0000599 Johnson-Corey-Chaykovsky epoxide synthesis http://purl.obolibrary.org/obo/RXNO_0000346 oxacycle synthesis Reaction of a sulfur ylide with a ketone to produce an epoxide. http://purl.obolibrary.org/obo/RXNO_0000600 Johnson-Corey-Chaykovsky cyclopropane synthesis http://purl.obolibrary.org/obo/RXNO_0000598 Johnson-Corey-Chaykovsky reaction Reaction of a sulfur ylide with an olefin to produce a cyclopropane. http://purl.obolibrary.org/obo/RXNO_0000601 Johnson-Corey-Chaykovsky aziridine synthesis http://purl.obolibrary.org/obo/RXNO_0000347 azacycle synthesis Reaction of a sulfur ylide with an imine to produce an aziridine. http://purl.obolibrary.org/obo/RXNO_0000602 Johnson-Corey-Chaykovsky thiirane synthesis http://purl.obolibrary.org/obo/RXNO_0000348 thiacycle synthesis Reaction of a sulfur ylide with a thione to produce a thiirane. http://purl.obolibrary.org/obo/RXNO_0000603 cross-coupling http://purl.obolibrary.org/obo/RXNO_0000000 molecular skeleton joining reaction A joining reaction where a carbon-carbon bond is formed between unlike moieties. http://purl.obolibrary.org/obo/RXNO_0000604 Liebeskind-Srogl coupling http://purl.obolibrary.org/obo/RXNO_0000603 cross-coupling A cross-coupling reaction where a thioester and a boronic acid react to form a ketone. It uses a metal catalyst. http://purl.obolibrary.org/obo/RXNO_0000605 Fukuyama coupling http://purl.obolibrary.org/obo/RXNO_0000603 cross-coupling A cross-coupling reaction where a thioester and an organozinc halide react to form a ketone. It uses a palladium catalyst. http://purl.obolibrary.org/obo/RXNO_0000606 chloride Finkelstein reaction http://purl.obolibrary.org/obo/RXNO_0000155 Finkelstein reaction The conversion of an alkyl chloride to an alkyl iodide by SN2 substitution.The reaction relies upon the equilibrium being pushed to completion by precipitation. http://purl.obolibrary.org/obo/RXNO_0000607 bromide Finkelstein reaction http://purl.obolibrary.org/obo/RXNO_0000155 Finkelstein reaction The conversion of an alkyl bromide to an alkyl iodide by SN2 substitution.The reaction relies upon the equilibrium being pushed to completion by precipitation. http://purl.obolibrary.org/obo/RXNO_0000608 sulfonate ester Finkelstein reaction http://purl.obolibrary.org/obo/RXNO_0000155 Finkelstein reaction The conversion of an alkyl sulfonate ester to an alkyl iodide by SN2 substitution.The reaction relies upon the equilibrium being pushed to completion by precipitation. http://purl.obolibrary.org/obo/RXNO_0000609 Sandmeyer fluorination http://purl.obolibrary.org/obo/RXNO_0000333 Sandmeyer halogenation An aromatic substitution reaction where an aryl diazonium salt reacts with a copper(I) fluoride to form an aromatic fluoride. http://purl.obolibrary.org/obo/RXNO_0000610 Sandmeyer chlorination http://purl.obolibrary.org/obo/RXNO_0000333 Sandmeyer halogenation An aromatic substitution reaction where an aryl diazonium salt reacts with a copper(I) chloride to form an aromatic chloride. http://purl.obolibrary.org/obo/RXNO_0000611 Sandmeyer bromination http://purl.obolibrary.org/obo/RXNO_0000333 Sandmeyer halogenation An aromatic substitution reaction where an aryl diazonium salt reacts with a copper(I) bromide to form an aromatic bromide. http://purl.obolibrary.org/obo/RXNO_0000612 Sandmeyer iodination http://purl.obolibrary.org/obo/RXNO_0000333 Sandmeyer halogenation An aromatic substitution reaction where an aryl diazonium salt reacts with a copper(I) iodide to form an aromatic iodide. http://purl.obolibrary.org/obo/RXNO_0000613 imidazole synthesis http://purl.obolibrary.org/obo/RXNO_0000347 azacycle synthesis A planned reaction in which one of the products contains an imidazole system that was not in any of the reactants. http://purl.obolibrary.org/obo/RXNO_0000614 indazole synthesis http://purl.obolibrary.org/obo/RXNO_0000347 azacycle synthesis A planned reaction in which one of the products contains an indazole system that was not in any of the reactants. http://purl.obolibrary.org/obo/RXNO_0000615 piperazine synthesis http://purl.obolibrary.org/obo/RXNO_0000347 azacycle synthesis A planned reaction in which one of the products contains a piperazine system that was not in any of the reactants. http://purl.obolibrary.org/obo/RXNO_0000616 piperidine synthesis http://purl.obolibrary.org/obo/RXNO_0000347 azacycle synthesis A planned reaction in which one of the products contains a piperidine system that was not in any of the reactants. http://purl.obolibrary.org/obo/RXNO_0000617 pyrrolidine synthesis http://purl.obolibrary.org/obo/RXNO_0000347 azacycle synthesis A planned reaction in which one of the products contains a pyrrolidine system that was not in any of the reactants. http://purl.obolibrary.org/obo/RXNO_0000618 Hofmann-Löffler-Freytag reaction http://purl.obolibrary.org/obo/RXNO_0000347 azacycle synthesis An azacycle synthesis in which pyrrolidines or piperidines are formed by decomposition of protonated N-haloamines. http://purl.obolibrary.org/obo/RXNO_0000619 Hofmann-Löffler-Freytag piperidine synthesis http://purl.obolibrary.org/obo/RXNO_0000616 piperidine synthesis A Hofmann-Löffler-Freytag reaction in which the product is a piperidine. http://purl.obolibrary.org/obo/RXNO_0000620 Hofmann-Löffler-Freytag pyrrolidine synthesis http://purl.obolibrary.org/obo/RXNO_0000617 pyrrolidine synthesis A Hofmann-Löffler-Freytag reaction in which the product is a pyrrolidine. http://purl.obolibrary.org/obo/CHEBI_50047 organic amino compound http://purl.obolibrary.org/obo/CHEBI_35352 organonitrogen compound A compound formally derived from ammonia by replacing one, two or three hydrogen atoms by organyl groups. http://purl.obolibrary.org/obo/CHEBI_16134 ammonia http://purl.obolibrary.org/obo/CHEBI_23367 molecular entity An azane that consists of a single nitrogen atom covelently bonded to three hydrogen atoms. http://purl.obolibrary.org/obo/CHEBI_17792 organohalogen compound http://purl.obolibrary.org/obo/CHEBI_37578 halide A compound containing at least one carbon-halogen bond (where X is a halogen atom). http://purl.obolibrary.org/obo/CHEBI_17997 dinitrogen http://purl.obolibrary.org/obo/CHEBI_23367 molecular entity An elemental molecule consisting of two trivalently-bonded nitrogen atoms. http://purl.obolibrary.org/obo/CHEBI_18291 manganese atom http://purl.obolibrary.org/obo/CHEBI_27081 transition element atom A manganese group element atom that has formula Mn. http://purl.obolibrary.org/obo/CHEBI_29312 sulfanyl http://purl.obolibrary.org/obo/CHEBI_23367 molecular entity A sulfur hydride that has formula HS. http://purl.obolibrary.org/obo/RXNO_0000670 Groebke-Blackburn-Bienaymé reaction http://purl.obolibrary.org/obo/RXNO_0000052 fused-ring-system formation A three-component reaction (3CR) of a heterocyclic amidine, an aldehyde, and an isocyanide, resulting in a cyclic compound with imidazo[1,2-a] heterocycle as the core structure. http://purl.obolibrary.org/obo/RXNO_0000671 Baeyer oxindole synthesis http://purl.obolibrary.org/obo/RXNO_0000052 fused-ring-system formation The preparation of oxindole/indolin-2-one from 2-nitrophenylacetic acid by reduction of the nitro group and subsequent dehydration. http://purl.obolibrary.org/obo/RXNO_0000672 Leimgruber-Batcho indole synthesis http://purl.obolibrary.org/obo/RXNO_0000395 indole synthesis Condensation of a formamide acetal with a derivative of o-nitrotoluene to yield an enamine intermediate that subsequently undergoes reductive cyclization to give the corresponding indole. http://purl.obolibrary.org/obo/RXNO_0000674 decarboxylative cross-coupling http://purl.obolibrary.org/obo/RXNO_0000603 cross-coupling A chemical reaction in which a carboxylic acid (or its salt) reacts with an organic (alkyl or aryl) halide to form a new carbon-carbon bond with concomitant loss of CO2. In addition, the reaction requires a metal catalyst, a base and an oxidizing agent. http://purl.obolibrary.org/obo/RXNO_0000675 Balsohn alkylation http://purl.obolibrary.org/obo/RXNO_0000002 carbon-carbon coupling reaction A carbon-carbon coupling reaction between an arene and an alkene to give a substituted arene. The reaction is catalysed by a Lewis acid. http://purl.obolibrary.org/obo/RXNO_0000676 Kabachnik-Fields reaction http://purl.obolibrary.org/obo/MOP_0000628 molecular dehydration reaction A three-component condensation reaction in which primary or secondary amines react with a carbonyl compound (aldehyde or ketone) and a dialkyl phosphonate (also called dialkyl phosphite) to form an alpha-aminophosphonate. http://purl.obolibrary.org/obo/RXNO_0000677 Baekeland-Manasse-Lederer reaction http://purl.obolibrary.org/obo/RXNO_0000246 polymerisation reaction A polymerisation reaction in which phenol and formaldehyde react together in a chain reaction to form a phenol formaldehyde resin (also infrequently called phenoplast). http://purl.obolibrary.org/obo/RXNO_0000678 Aston-Greenburg rearrangement http://purl.obolibrary.org/obo/RXNO_0000025 rearrangement step The rearrangement of an alpha-haloketone into an ester with a tertiary alpha-carbon atom by intramolecular migration of an alkyl or aryl group. http://purl.obolibrary.org/obo/RXNO_0000679 Baddeley isomerization http://purl.obolibrary.org/obo/RXNO_0000025 rearrangement step The rearrangement/migration of alkyl groups in polyalkylbenzenes or polynuclear aromatic compounds in the presence of anhydrous aluminum chloride or the mixture of protonic acid and Lewis acid. http://purl.obolibrary.org/obo/RXNO_0000681 Dötz reaction http://purl.obolibrary.org/obo/RXNO_0000005 ring formation reaction step A three component cyclization of an aromatic or vinylic alkoxy pentacarbonyl chromium carbene complex, an alkyne and carbon monoxide to give a Cr(CO)3 coordinated phenol. http://purl.obolibrary.org/obo/RXNO_0000682 Kulinkovich reaction http://purl.obolibrary.org/obo/RXNO_0000005 ring formation reaction step The formation of a substituted cyclopropanol by reaction of a carboxylic ester with a Grignard reagent (carrying a hydrogen atom in the beta-position) in the presence of a titanium(IV) alkoxide as catalyst. A modified cyclopropanol product can be generated by addition of a terminal alkene as a further reactant. http://purl.obolibrary.org/obo/RXNO_0000683 Kulinkovich-de Meijere reaction http://purl.obolibrary.org/obo/RXNO_0000005 ring formation reaction step The formation of a substituted cyclopropylamine by reaction of an amide with a Grignard reagent (carrying a hydrogen atom in the beta-position) in the presence of a titanium(IV) alkoxide as catalyst. http://purl.obolibrary.org/obo/RXNO_0000684 Kulinkovich-Szymoniak reaction http://purl.obolibrary.org/obo/RXNO_0000005 ring formation reaction step The formation of a substituted primary cyclopropylamine by reaction of a nitrile with a Grignard reagent (carrying a hydrogen atom in the beta-position) in the presence of a titanium(IV) alkoxide as catalyst. http://purl.obolibrary.org/obo/RXNO_0000686 Jacobsen epoxidation http://purl.obolibrary.org/obo/MOP_0000671 epoxidation Chiral (salen)manganese(III)-catalyzed asymmetric epoxidation of alkenes. In addition to the catalyst, stoichiometric amounts of an oxidant (e.g. sodium hypochlorite) are required. http://purl.obolibrary.org/obo/RXNO_0000687 Shi epoxidation http://purl.obolibrary.org/obo/MOP_0000671 epoxidation Organocatalytic enantioselective epoxidation of trans- and tri-substituted olefins using a fructose derived chiral ketone catalyst and potassium peroxomonosulfate or H2O2 as an oxidant. http://purl.obolibrary.org/obo/RXNO_0000688 Asinger reaction http://purl.obolibrary.org/obo/RXNO_0000348 thiacycle synthesis A multicomponent reaction (A-4CR) in which 3-thiazolines (2,5-dihydro-1,3-thiazoles) or mixtures of several 3-thiazolines are synthesized from elemental sulfur, an alpha-substitutable ketone or aldehyde, another carbonyl component and ammonia. http://purl.obolibrary.org/obo/RXNO_0000689 haloform reaction http://purl.obolibrary.org/obo/MOP_0000550 halogenation Cleavage of methyl ketones (i.e. oxidative demethylation) with halogens (or hypohalites) in the presence of a base to give a carboxylic acid and haloform (trihalomethane). http://purl.obolibrary.org/obo/RXNO_0000690 Atherton-Todd reaction http://purl.obolibrary.org/obo/MOP_0000550 halogenation The conversion of dialkyl phosphites (dialkyl phosphonates) to dialkyl chlorophosphates using tetrachloromethane and a base (usually a primary, secondary or tertiary amine). http://purl.obolibrary.org/obo/RXNO_0000691 Baeyer diarylmethane synthesis http://purl.obolibrary.org/obo/MOP_0000628 molecular dehydration reaction Synthesis of diarylmethane derivatives using an aldehyde and an aromatic compound at low temperature in an acidic medium. http://purl.obolibrary.org/obo/RXNO_0000692 silyl deprotection http://purl.obolibrary.org/obo/RXNO_0000430 hydroxy group deprotection A hydroxyl group deprotection in which an silyl ether group is transformed into a hydroxy group. http://purl.obolibrary.org/obo/CHEBI_22712 benzenes http://purl.obolibrary.org/obo/CHEBI_33836 benzenoid aromatic compound Any benzenoid aromatic compound consisting of the benzene skeleton and its substituted derivatives. http://purl.obolibrary.org/obo/CHEBI_38976 alkylbenzene http://purl.obolibrary.org/obo/CHEBI_33847 monocyclic arene A monocyclic arene that is benzene substituted with one or more alkyl groups. http://purl.obolibrary.org/obo/CHEBI_48901 thiazoles http://purl.obolibrary.org/obo/CHEBI_68452 azole An azole in which the five-membered heterocyclic aromatic skeleton contains a N atom and one S atom. http://purl.obolibrary.org/obo/CHEBI_60027 polymer http://purl.obolibrary.org/obo/CHEBI_60004 mixture A polymer is a mixture, which is composed of macromolecules of different kinds and which may be differentiated by composition, length, degree of branching etc.. http://purl.obolibrary.org/obo/CHEBI_33655 aromatic compound http://purl.obolibrary.org/obo/CHEBI_33595 cyclic compound A cyclically conjugated molecular entity with a stability (due to delocalization) significantly greater than that of a hypothetical localized structure (e.g. Kekule structure) is said to possess aromatic character. http://purl.obolibrary.org/obo/CHEBI_35701 ester http://purl.obolibrary.org/obo/CHEBI_36963 organooxygen compound A compound formally derived from an oxoacid RkE(=O)l(OH)m (l > 0) and an alcohol, phenol, heteroarenol, or enol by linking with formal loss of water from an acidic hydroxy group of the former and a hydroxy group of the latter. http://purl.obolibrary.org/obo/CHEBI_37735 phosphonic ester http://purl.obolibrary.org/obo/CHEBI_35701 ester A phosphonic acid derivative in which one or both OH groups have been esterified. http://purl.obolibrary.org/obo/CHEBI_23424 cyanides http://purl.obolibrary.org/obo/CHEBI_35352 organonitrogen compound Salts and C-organyl derivatives of hydrogen cyanide, HC#N. http://purl.obolibrary.org/obo/CHEBI_35353 isocyanide http://purl.obolibrary.org/obo/CHEBI_35352 organonitrogen compound The isomer HN(+)#C(-) of hydrocyanic acid, HC#N, and its hydrocarbyl derivatives RNC (RN(+)#C(-)). http://purl.obolibrary.org/obo/CHEBI_37578 halide http://purl.obolibrary.org/obo/CHEBI_23367 molecular entity Any heteroatomic molecular entity that is a chemical compound of halogen with other chemical elements. http://purl.obolibrary.org/obo/CHEBI_39279 halomethane http://purl.obolibrary.org/obo/CHEBI_24469 haloalkane A haloalkane that is methane in which one (or more) of the hydrogens have been replaced by a halogen atom/halogen atoms. http://purl.obolibrary.org/obo/CHEBI_31697 indolin-2-one http://purl.obolibrary.org/obo/CHEBI_24828 indoles An indolinone carrying an oxo group at position 2. http://purl.obolibrary.org/obo/CHEBI_33597 homocyclic compound http://purl.obolibrary.org/obo/CHEBI_33595 cyclic compound A cyclic compound having as ring members atoms of the same element only. http://purl.obolibrary.org/obo/CHEBI_33671 heteropolycyclic compound http://purl.obolibrary.org/obo/CHEBI_33635 polycyclic compound A polycyclic compound in which at least one of the rings contains at least one non-carbon atom. http://purl.obolibrary.org/obo/CHEBI_33847 monocyclic arene http://purl.obolibrary.org/obo/CHEBI_33658 arene A monocyclic aromatic hydrocarbon. http://purl.obolibrary.org/obo/CHEBI_33848 polycyclic arene http://purl.obolibrary.org/obo/CHEBI_33658 arene A polycyclic aromatic hydrocarbon. http://purl.obolibrary.org/obo/CHEBI_39477 aminoxyls http://purl.obolibrary.org/obo/CHEBI_36872 organic radical Radicals derived from hydroxylamines by removal of the hydrogen atom from the hydroxy group. The synonymous terms nitroxyl radicals and nitroxides erroneously suggest the presence of a nitro group. http://purl.obolibrary.org/obo/CHEBI_44864 propane-1,3-dithiol http://purl.obolibrary.org/obo/CHEBI_29256 thiol A dithiol that is propane substituted by thiol groups at positions 1 ans 3. http://purl.obolibrary.org/obo/CHEBI_47986 silyl enol ether http://purl.obolibrary.org/obo/CHEBI_47985 enol ether Enol ethers ROR' where R' has the structure SiR''R'''R''''. http://purl.obolibrary.org/obo/CHEBI_47988 silyl ether http://purl.obolibrary.org/obo/CHEBI_25713 organosilicon compound Ethers ROR' where R' has the structure SiR''R'''R''''. http://purl.obolibrary.org/obo/CHEBI_59999 chemical substance http://purl.obolibrary.org/obo/CHEBI_24431 chemical entity A chemical substance is a portion of matter of constant composition, composed of molecular entities of the same type or of different types. http://purl.obolibrary.org/obo/CHEBI_51186 organolithium compound http://purl.obolibrary.org/obo/CHEBI_25707 organometallic compound A compound containing at least one carbon-lithium bond. http://purl.obolibrary.org/obo/CHEBI_51187 organomagnesium compound http://purl.obolibrary.org/obo/CHEBI_25707 organometallic compound A compound containing at least one carbon-magnesium bond. http://purl.obolibrary.org/obo/CHEBI_51462 alkyllithium compound http://purl.obolibrary.org/obo/CHEBI_51186 organolithium compound An organolithium compound where an alkyl group is bound to a lithium atom. http://purl.obolibrary.org/obo/CHEBI_51469 butyllithium http://purl.obolibrary.org/obo/CHEBI_51462 alkyllithium compound An alkyllithium compound that has formula C4H9Li. http://purl.obolibrary.org/obo/CHEBI_51494 organozinc compound http://purl.obolibrary.org/obo/CHEBI_25707 organometallic compound A compound containing at least one carbon-zinc bond. http://purl.obolibrary.org/obo/CHEBI_51839 alpha-haloketone http://purl.obolibrary.org/obo/CHEBI_17087 ketone A haloketone in which the halogen and oxo substituents are on adjacent carbon atoms. http://purl.obolibrary.org/obo/CHEBI_52395 oxyketone http://purl.obolibrary.org/obo/CHEBI_17087 ketone A compound with the general formula R2C=O (R=/=H) where one or more of the R groups contains an oxy (-O-) group. http://purl.obolibrary.org/obo/MOP_0000714 carbonyl oxidation to alkyne http://purl.obolibrary.org/obo/MOP_0000568 oxidation Oxidation of a carbonyl group to an alkyne. http://purl.obolibrary.org/obo/MOP_0000715 [3+2] cycloaddition http://purl.obolibrary.org/obo/MOP_0000562 cycloaddition A cycloaddition in which one participant contributes three electrons and the other participant contributes two electrons to the transformation of reactants to products. http://purl.obolibrary.org/obo/MOP_0000716 enolisation http://purl.obolibrary.org/obo/MOP_0000543 molecular process Molecular process in which an aldehyde or ketone tautomerises to form an enol. http://purl.obolibrary.org/obo/MOP_0000717 enolisability http://purl.obolibrary.org/obo/BFO_0000016 disposition Disposition that is realised in the process of enolisation http://purl.obolibrary.org/obo/MOP_0000718 enolisable carbonyl compound http://purl.obolibrary.org/obo/CHEBI_36587 carbonyl compound A carbonyl compound that bears the disposition to be enolised. http://purl.obolibrary.org/obo/MOP_0000719 O-dealkylation http://purl.obolibrary.org/obo/MOP_0001369 dealkylation Breaking of a covalent bond between an alkyl group and an oxygen atom. http://purl.obolibrary.org/obo/MOP_0000720 [2+2+1] cycloaddition http://purl.obolibrary.org/obo/MOP_0000562 cycloaddition A cycloaddition in which two participants contribute two electrons and the other participant contributes one electron to the transformation of reactants to products. http://purl.obolibrary.org/obo/MOP_0000722 decarboxylative condensation http://purl.obolibrary.org/obo/MOP_0000627 condensation reaction A reaction in which two or more reactants or remote reactive sites within the same molecular entity yield a single main product with accompanying formation of a carbon dioxide molecule. http://purl.obolibrary.org/obo/MOP_0000723 deethanolative condensation http://purl.obolibrary.org/obo/MOP_0000825 dealcoholative condensation A reaction in which two or more reactants or remote reactive sites within the same molecular entity yield a single main product with accompanying formation of an ethanol molecule. http://purl.obolibrary.org/obo/MOP_0001713 decarboxylation http://purl.obolibrary.org/obo/MOP_0001458 deorganylation Breaking of a covalent bond between a molecule and a carboxy group. http://purl.obolibrary.org/obo/MOP_0006369 P-alkylation http://purl.obolibrary.org/obo/MOP_0000369 alkylation The formation of a covalent bond between a phosphorus atom and an alkyl group. http://purl.obolibrary.org/obo/RXNO_0000000 molecular skeleton joining reaction http://purl.obolibrary.org/obo/RXNO_0000002 carbon-carbon coupling reaction A reaction where the number of atoms in the molecular skeleton increases. http://purl.obolibrary.org/obo/RXNO_0000001 planned reaction step http://purl.obolibrary.org/obo/OBI_0000011 planned process A molecular process with which the experimenters aim to achieve a particular molecular transformation. http://purl.obolibrary.org/obo/RXNO_0000002 carbon-carbon coupling reaction http://purl.obolibrary.org/obo/MOP_0000543 molecular process A reaction where a bond is formed between two carbon atoms. http://purl.obolibrary.org/obo/RXNO_0000003 Perkin reaction http://purl.obolibrary.org/obo/RXNO_0000017 aldol condensation An aldol condensation where an aryl aldehyde reacts with an acid anhydride to form a cinnamic acid. http://purl.obolibrary.org/obo/RXNO_0000005 ring formation reaction step http://purl.obolibrary.org/obo/MOP_0000561 cyclization A planned reaction step where the product contains a ring that was not in any of the reactants. http://purl.obolibrary.org/obo/RXNO_0000006 Diels-Alder reaction http://purl.obolibrary.org/obo/MOP_0000565 [4+2] cycloaddition A [4+2] cycloaddition reaction where a diene reacts with a compound containing a double or triple bond (a dienophile) to form an unsaturated six-membered ring compound. http://purl.obolibrary.org/obo/RXNO_0000007 ene reaction http://purl.obolibrary.org/obo/RXNO_0000000 molecular skeleton joining reaction A joining reaction where an alkene with an allylic hydrogen reacts with a compound containing a multiple bond (an enophile) to form a substituted alkene. http://purl.obolibrary.org/obo/RXNO_0000008 conjugate addition http://purl.obolibrary.org/obo/RXNO_0000000 molecular skeleton joining reaction A joining reaction where a nucleophile adds to the beta-carbon of an alpha,beta-unsaturated system (or an activated carbon-carbon bond). http://purl.obolibrary.org/obo/RXNO_0000009 Michael addition http://purl.obolibrary.org/obo/RXNO_0000008 conjugate addition A conjugate addition reaction where a carbon nucleophile adds to the beta-carbon of an alpha,beta-unsaturated system (or an activated carbon-carbon bond). http://purl.obolibrary.org/obo/RXNO_0000010 functional modification http://purl.obolibrary.org/obo/RXNO_0000001 planned reaction step A reaction where the number of atoms in the skeleton, and their connectivity, remain the same. http://purl.obolibrary.org/obo/RXNO_0000011 functional group modification http://purl.obolibrary.org/obo/RXNO_0000010 functional modification A reaction in which a functional group undergoes a change that does not affect the number of atoms in (or connectivity of) the skeleton of the molecule. http://purl.obolibrary.org/obo/RXNO_0000012 functional group oxidation http://purl.obolibrary.org/obo/MOP_0000568 oxidation A functional group modification reaction where a functional group is oxidised. http://purl.obolibrary.org/obo/RXNO_0000013 diazotisation http://purl.obolibrary.org/obo/RXNO_0000012 functional group oxidation A functional group oxidation where an aromatic amine is transformed into an aromatic diazonium salt. http://purl.obolibrary.org/obo/RXNO_0000014 Grignard reaction http://purl.obolibrary.org/obo/RXNO_0000000 molecular skeleton joining reaction A carbon-carbon coupling reaction where a Grignard reagent reacts with a compound containing an electrophilic carbon atom. A Grignard reagent is a magnesium-stabilised carbon nucleophile. An aldehyde leads to a secondary alcohol, a ketone leads to a tertiary alcohol, an ester leads to a ketone and a nitrile leads to a ketone. http://purl.obolibrary.org/obo/RXNO_0000015 Wittig reaction http://purl.obolibrary.org/obo/RXNO_0000479 olefination A carbon-carbon coupling reaction where a carbonyl compound reacts with a phosphonium ylide to give an alkene. http://purl.obolibrary.org/obo/RXNO_0000016 aldol addition http://purl.obolibrary.org/obo/RXNO_0000000 molecular skeleton joining reaction A carbon-carbon coupling reaction where an enol or enolate reacts with a carbonyl compound to form a beta-hydroxy ketone. The name comes from aldehyde + alcohol. http://purl.obolibrary.org/obo/RXNO_0000017 aldol condensation http://purl.obolibrary.org/obo/MOP_0000628 molecular dehydration reaction An aldol addition where an enol or enolate reacts with a carbonyl compound to form an alpha,beta-unsaturated ketone. http://purl.obolibrary.org/obo/RXNO_0000018 1,3-dipolar cycloaddition http://purl.obolibrary.org/obo/MOP_0000562 cycloaddition A ring formation reaction where a 1,3-dipolar compound reacts with an alkene or alkyne to form a five-membered ring compound. http://purl.obolibrary.org/obo/RXNO_0000021 Sandmeyer reaction http://purl.obolibrary.org/obo/RXNO_0000332 aromatic substitution step An aromatic substitution reaction where an aryl diazonium salt reacts with a copper(I) halide or pseudohalide to form an aromatic halide or pseudohalide. http://purl.obolibrary.org/obo/RXNO_0000022 Gattermann halogenation http://purl.obolibrary.org/obo/MOP_0000550 halogenation An aromatic substitution reaction where an aryl diazonium salt reacts with copper powder and hydrochloric acid or hydrobromic acid to form an aromatic chloride or bromide. http://purl.obolibrary.org/obo/RXNO_0000023 Koerner-Contardi reaction http://purl.obolibrary.org/obo/RXNO_0000332 aromatic substitution step An aromatic substitution reaction where an aryl diazonium salt reacts with a copper(II) halide to form an aromatic halide. http://purl.obolibrary.org/obo/RXNO_0000025 rearrangement step http://purl.obolibrary.org/obo/RXNO_0000001 planned reaction step A reaction which preserves the number of rings and number of skeletal atoms and in which the molecule rearranges so that one or more atoms or groups of atoms move from one atom to another. http://purl.obolibrary.org/obo/RXNO_0000026 Beckmann rearrangement http://purl.obolibrary.org/obo/RXNO_0000025 rearrangement step A rearrangement where an oxime rearranges to form an amide. Often there is selective migration of one group. http://purl.obolibrary.org/obo/RXNO_0000028 Cope rearrangement http://purl.obolibrary.org/obo/MOP_0000721 [3,3]-sigmatropic rearrangement A [3,3]-sigmatropic rearrangement where a 1,5-hexadiene rearranges to form a 1,5-hexadiene. http://purl.obolibrary.org/obo/RXNO_0000029 oxy-Cope rearrangement http://purl.obolibrary.org/obo/MOP_0000721 [3,3]-sigmatropic rearrangement A [3,3]-sigmatropic rearrangement of a 3-hydroxy-1,5-hexadiene rearranges to form a 5,6-unsaturated carbonyl compound. http://purl.obolibrary.org/obo/RXNO_0000030 molecular skeleton insertion reaction http://purl.obolibrary.org/obo/RXNO_0000000 molecular skeleton joining reaction A joining reaction in which one or more atoms are added to the middle of a chain. http://purl.obolibrary.org/obo/RXNO_0000031 Baeyer-Villiger oxidation http://purl.obolibrary.org/obo/RXNO_0000030 molecular skeleton insertion reaction A reaction of a ketone to give an ester, in which an alkyl, benzyl or phenyl group migrates from one of the alpha-carbon centres to an adjacent oxygen, displacing an oxygen-based leaving group; the result is a formal insertion of an oxygen atom. The reaction also works with aldehydes, giving the corresponding carboxylic acid. The term "Baeyer-Villiger rearrangement" may occasionally be used in a mechanistic sense to refer specificially to the actual rearrangement step. http://purl.obolibrary.org/obo/RXNO_0000032 Mannich reaction http://purl.obolibrary.org/obo/RXNO_0000000 molecular skeleton joining reaction A carbon-carbon coupling reaction where ammonia or an amine reacts with a non-enolisable aldehyde, often methanal, and an enolisable carbonyl compound to form a beta-amino carbonyl compound. http://purl.obolibrary.org/obo/RXNO_0000034 Mitsunobu reaction http://purl.obolibrary.org/obo/RXNO_0000331 substitution step A substitution where an alcohol is converted into something else. Typical reagents are a dialkyl azodicarboxylate and a triarylphosphine. The alcohol stereocentre is inverted. http://purl.obolibrary.org/obo/RXNO_0000035 Stille coupling http://purl.obolibrary.org/obo/RXNO_0000000 molecular skeleton joining reaction A carbon-carbon coupling reaction where a stannane reacts with an organohalide or organotriflate. http://purl.obolibrary.org/obo/RXNO_0000036 Reformatsky reaction http://purl.obolibrary.org/obo/RXNO_0000002 carbon-carbon coupling reaction A carbon-carbon coupling reaction where an aldehyde or amine reacts with a alpha-halo ester and zinc to form a beta-hydroxy ester. http://purl.obolibrary.org/obo/RXNO_0000037 functional group reduction http://purl.obolibrary.org/obo/RXNO_0000011 functional group modification A functional group modification reaction where a functional group is reduced. http://purl.obolibrary.org/obo/RXNO_0000038 Clemmensen reduction http://purl.obolibrary.org/obo/RXNO_0000037 functional group reduction A functional group reduction where an aldehyde or ketone carbonyl group is reduced to a methylene with zinc-mercury amalgam and hydrochloric acid. http://purl.obolibrary.org/obo/RXNO_0000039 carbon-carbon homocoupling reaction http://purl.obolibrary.org/obo/RXNO_0000002 carbon-carbon coupling reaction A joining reaction where a carbon-carbon bond is formed between like moieties. http://purl.obolibrary.org/obo/RXNO_0000040 Ullmann reaction http://purl.obolibrary.org/obo/RXNO_0000039 carbon-carbon homocoupling reaction A carbon-carbon homocoupling reaction of an aryl halide mediated by copper. http://purl.obolibrary.org/obo/RXNO_0000041 addition reaction step http://purl.obolibrary.org/obo/RXNO_0000011 functional group modification A reaction in which two or more groups of atoms are added to the molecule, resulting in a change of skeletal bond order. http://purl.obolibrary.org/obo/RXNO_0000042 Birch reduction http://purl.obolibrary.org/obo/RXNO_0000041 addition reaction step Addition of hydrogen atoms to aromatic rings by means of alkali metals in liquid ammonia. http://purl.obolibrary.org/obo/RXNO_0000043 Claisen condensation http://purl.obolibrary.org/obo/RXNO_0000000 molecular skeleton joining reaction A carbon-carbon coupling reaction of an ester and a carbonyl compound to form a beta-keto ester. http://purl.obolibrary.org/obo/RXNO_0000044 Knoevenagel condensation http://purl.obolibrary.org/obo/RXNO_0000000 molecular skeleton joining reaction A carbon-carbon coupling reaction of an aldehyde and a methylene compound. http://purl.obolibrary.org/obo/RXNO_0000045 Friedel-Crafts acylation http://purl.obolibrary.org/obo/RXNO_0000369 Friedel-Crafts reaction A carbon-carbon coupling reaction between an arene and a carbonyl compound (usually an acyl halide) to give an aryl ketone. The reaction is catalysed by a Lewis acid. http://purl.obolibrary.org/obo/RXNO_0000046 Friedel-Crafts alkylation http://purl.obolibrary.org/obo/RXNO_0000369 Friedel-Crafts reaction A carbon-carbon coupling reaction between an arene and an alkyl halide/alkene/alcohol (anything that can form a carbocation) to give a substituted arene. The reaction is catalysed by a Lewis acid. http://purl.obolibrary.org/obo/RXNO_0000047 Oppenauer oxidation http://purl.obolibrary.org/obo/RXNO_0000012 functional group oxidation An oxidation of a secondary alcohol to a ketone involving an equilibrium between the alcohol and a reagent ketone present in excess, catalysed by a metal alkoxide. http://purl.obolibrary.org/obo/RXNO_0000048 Prins reaction http://purl.obolibrary.org/obo/RXNO_0000000 molecular skeleton joining reaction A carbon-carbon coupling between formaldehyde and an alkene to give a 1,3-diol or an allylic alcohol, catalysed by acid. http://purl.obolibrary.org/obo/RXNO_0000049 intramolecular Prins reaction http://purl.obolibrary.org/obo/RXNO_0000005 ring formation reaction step A reaction between formaldehyde and an alkene to give a 1,3-dioxane, catalysed by acid. http://purl.obolibrary.org/obo/RXNO_0000050 pinacol rearrangement http://purl.obolibrary.org/obo/RXNO_0000025 rearrangement step A rearrangement of a 1,2-diol to give a carbonyl compound, catalysed by acid. http://purl.obolibrary.org/obo/RXNO_0000051 Wolff rearrangement http://purl.obolibrary.org/obo/RXNO_0000025 rearrangement step A rearrangement of a diazoketone to give a ketene, with the elimination of molecular nitrogen. http://purl.obolibrary.org/obo/RXNO_0000052 fused-ring-system formation http://purl.obolibrary.org/obo/RXNO_0000005 ring formation reaction step A reaction in which a fused ring system is present in a product that was not present in any of the reactants. http://purl.obolibrary.org/obo/RXNO_0000053 Bischler-Napieralski reaction http://purl.obolibrary.org/obo/RXNO_0000052 fused-ring-system formation A cyclodehydration of a beta-phenethylamide to give a 3,4-dihydroisoquinoline. http://purl.obolibrary.org/obo/RXNO_0000054 Curtius rearrangement http://purl.obolibrary.org/obo/RXNO_0000025 rearrangement step A rearrangement of an acyl azide to give an isocyanate by pyrolysis, with the elimination of molecular nitrogen. http://purl.obolibrary.org/obo/RXNO_0000055 Vilsmeier-Haack reaction http://purl.obolibrary.org/obo/MOP_0000003 formylation A formylation of an activated arene with a disubstituted formamide to give an arenecarbaldehyde. http://purl.obolibrary.org/obo/RXNO_0000056 Horner-Wadsworth-Emmons reaction http://purl.obolibrary.org/obo/RXNO_0000479 olefination A carbon-carbon coupling reaction between a phosphonate and a carbonyl compound to give an olefin. http://purl.obolibrary.org/obo/RXNO_0000057 Horner reaction http://purl.obolibrary.org/obo/RXNO_0000479 olefination A joining reaction between a phosphine oxide and a carbonyl compound to give an olefin. http://purl.obolibrary.org/obo/RXNO_0000058 Ritter reaction http://purl.obolibrary.org/obo/RXNO_0000011 functional group modification A reaction between an alcohol or alkene and a nitrile to give an amide, catalysed by a Bronsted acid. http://purl.obolibrary.org/obo/RXNO_0000059 Pictet-Spengler reaction http://purl.obolibrary.org/obo/MOP_0000627 condensation reaction A condensation-cyclisation of a beta-phenethylamine with an aldehyde to give a tetrahydroisoquinoline. http://purl.obolibrary.org/obo/RXNO_0000060 Arbuzov reaction http://purl.obolibrary.org/obo/RXNO_0000331 substitution step The alkylation of a trialkyl phosphite with an alkyl halide or acyl halide to give an alkyl phosphonate. http://purl.obolibrary.org/obo/RXNO_0000061 Mukaiyama aldol condensation http://purl.obolibrary.org/obo/RXNO_0000017 aldol condensation An aldol condensation between an aldehyde or ketone and a silyl enol ether (also known as a ketene silyl acetal) to give a beta-hydroxy carbonyl compound. http://purl.obolibrary.org/obo/RXNO_0000062 Skraup reaction http://purl.obolibrary.org/obo/MOP_0000628 molecular dehydration reaction A condensation between an aromatic amine and glycerol to give a quinoline. http://purl.obolibrary.org/obo/RXNO_0000063 Arndt-Eistert reaction http://purl.obolibrary.org/obo/RXNO_0000030 molecular skeleton insertion reaction A homologation reaction of a carboxylic acid to give the homologated carboxylic acid via acyl chloride and diazoketone intermediates. http://purl.obolibrary.org/obo/RXNO_0000064 Fischer indole synthesis http://purl.obolibrary.org/obo/RXNO_0000395 indole synthesis Reaction of an aldehyde or ketone with a phenylhydrazine to give an indole. http://purl.obolibrary.org/obo/RXNO_0000065 Dieckmann cyclisation http://purl.obolibrary.org/obo/RXNO_0000005 ring formation reaction step An intramolecular cyclisation of a diester to give a cyclic beta-ketoester. http://purl.obolibrary.org/obo/RXNO_0000066 Staudinger reaction http://purl.obolibrary.org/obo/RXNO_0000000 molecular skeleton joining reaction A joining of an organic azide and a tertiary phosphine to give a phosphazo compound. http://purl.obolibrary.org/obo/RXNO_0000067 benzidine rearrangement http://purl.obolibrary.org/obo/RXNO_0000093 extrusion reaction A rearrangement of a hydrazobenzene to give a diaminobiphenyl compound. http://purl.obolibrary.org/obo/RXNO_0000068 semidine rearrangement http://purl.obolibrary.org/obo/RXNO_0000093 extrusion reaction A rearrangement of a p-substituted hydrazobenzene to give a p-aminodiphenylamine. http://purl.obolibrary.org/obo/RXNO_0000069 Dimroth rearrangement http://purl.obolibrary.org/obo/RXNO_0000202 ring rearrangement A rearrangement of a heterocyclic compound in which endocyclic and exocyclic heteroatoms swap places. http://purl.obolibrary.org/obo/RXNO_0000070 chain lengthening http://purl.obolibrary.org/obo/RXNO_0000000 molecular skeleton joining reaction A molecular skeleton joining reaction in which a chain part of a molecular skeleton is lengthened. http://purl.obolibrary.org/obo/RXNO_0000071 Edman degradation http://purl.obolibrary.org/obo/RXNO_0000517 terminal amino-acid residue cleaving reaction A cleaving reaction in which a peptide is treated with phenylisothiocyanate, removing the terminal amino acid group, to form the chain-shortened amine and a phenylthiohydantoin. http://purl.obolibrary.org/obo/RXNO_0000072 Reimer-Tiemann reaction http://purl.obolibrary.org/obo/MOP_0000003 formylation A formylation reaction between a phenol and chloroform (for example, to form an ortho-formyl phenol). http://purl.obolibrary.org/obo/RXNO_0000073 cleaving reaction http://purl.obolibrary.org/obo/RXNO_0000001 planned reaction step A reaction where atoms are lost from the molecular skeleton. http://purl.obolibrary.org/obo/RXNO_0000074 Wurtz reaction http://purl.obolibrary.org/obo/RXNO_0000039 carbon-carbon homocoupling reaction A carbon-carbon homocoupling reaction of two molecules of an alkyl halide with sodium to give a symmetrical product. http://purl.obolibrary.org/obo/RXNO_0000075 benzilic acid rearrangement http://purl.obolibrary.org/obo/RXNO_0000025 rearrangement step A rearrangement of a 1,2-diketone to an alpha-hydroxy carboxylic acid. It can also be applied to alpha-keto aldehydes. The first exmaple of this reaction was with benzil (PhC(=O)C(=O)Ph) to form benzilic acid, hence the name. http://purl.obolibrary.org/obo/RXNO_0000076 Baylis-Hillman reaction http://purl.obolibrary.org/obo/RXNO_0000000 molecular skeleton joining reaction A carbon-carbon coupling of an aldehyde to an activated alkene in the presence of a nucleophilic base to give an alpha-hydroxyalkylated compound. http://purl.obolibrary.org/obo/RXNO_0000077 Darzens reaction http://purl.obolibrary.org/obo/RXNO_0000000 molecular skeleton joining reaction A coupling of an aldehyde or ketone with an alpha-halo ester to form an alpha,beta-epoxy ester, which hydrolyses to yield aldehydes or ketones by elimination of carbon dioxide. http://purl.obolibrary.org/obo/RXNO_0000078 protection reaction http://purl.obolibrary.org/obo/RXNO_0000010 functional modification A reaction in which a functional group is modified by converting it into a protecting group, in order to make subsequent reactions more selective. http://purl.obolibrary.org/obo/RXNO_0000079 Boc protection http://purl.obolibrary.org/obo/RXNO_0000321 amino group protection A protection reaction in which an amine is converted into a tert-butoxycarbonyl compound. http://purl.obolibrary.org/obo/RXNO_0000080 Peterson olefination http://purl.obolibrary.org/obo/RXNO_0000479 olefination A carbon-carbon coupling reaction in which an alpha-silyl carbanion reacts with an aldehyde or a ketone to give an alkene, proceeding via a beta-hydroxysilane. The stereochemistry of the alkene can be controlled by treating the intermediate with acid or base. http://purl.obolibrary.org/obo/RXNO_0000081 Ullmann condensation http://purl.obolibrary.org/obo/RXNO_0000332 aromatic substitution step A coupling reaction in which a phenol is coupled to an aryl halide to give a diaryl ether in the presence of a copper compound. http://purl.obolibrary.org/obo/RXNO_0000082 Goldberg reaction http://purl.obolibrary.org/obo/RXNO_0000332 aromatic substitution step A coupling reaction in which an acetanilide is coupled to an aryl halide to give an N-acetyl diaryl amine in the presence of a copper compound. http://purl.obolibrary.org/obo/RXNO_0000083 Paternò–Büchi reaction http://purl.obolibrary.org/obo/MOP_0000563 [2+2] cycloaddition A photochemical cycloaddition between an aldehyde or ketone and an alkene to give an oxetane. http://purl.obolibrary.org/obo/RXNO_0000084 Barbier reaction http://purl.obolibrary.org/obo/RXNO_0000000 molecular skeleton joining reaction A joining reaction between an aldehyde or ketone and an alkyl halide or aryl halide or vinyl halide or allyl halide in the presence of metal to give a secondary or tertiary alcohol. http://purl.obolibrary.org/obo/RXNO_0000085 acyloin condensation http://purl.obolibrary.org/obo/RXNO_0000000 molecular skeleton joining reaction A reductive coupling reaction between two esters to give an acyloin (an alpha-hydroxyketone). http://purl.obolibrary.org/obo/RXNO_0000086 Henry reaction http://purl.obolibrary.org/obo/RXNO_0000002 carbon-carbon coupling reaction A carbon-carbon coupling reaction between a nitroalkane and an aldehyde or ketone to give a beta-hydroxy nitroalkane. http://purl.obolibrary.org/obo/RXNO_0000087 Barton reaction http://purl.obolibrary.org/obo/RXNO_0000025 rearrangement step The photolytic oxidation of a nitrate ester to give a gamma-nitroalcohol. http://purl.obolibrary.org/obo/RXNO_0000088 Negishi coupling http://purl.obolibrary.org/obo/RXNO_0000002 carbon-carbon coupling reaction A carbon-carbon coupling reaction between an organohalide or organotriflate and an organozinc compound. The reaction is catalysed by palladium or nickel. http://purl.obolibrary.org/obo/RXNO_0000089 Meerwein-Ponndorf-Verley reduction http://purl.obolibrary.org/obo/RXNO_0000037 functional group reduction A reduction of an aldehyde or ketone to an alcohol involving an equilibrium between the aldehyde or ketone and a reagent alcohol present in excess, catalysed by a metal alkoxide. This reaction is the reverse of the Oppenauer oxidation (RXNO:0000047). http://purl.obolibrary.org/obo/RXNO_0000090 Williamson ether synthesis http://purl.obolibrary.org/obo/RXNO_0000331 substitution step The reaction between an alkyl halide or alkyl sulfate and a metal alkoxide to give an ether. http://purl.obolibrary.org/obo/RXNO_0000091 Wittig methylenation http://purl.obolibrary.org/obo/RXNO_0000015 Wittig reaction A carbon-carbon coupling reaction where a carbonyl compound reacts with a phosphonium ylide to give a terminal alkene. http://purl.obolibrary.org/obo/RXNO_0000092 aza-Diels-Alder reaction http://purl.obolibrary.org/obo/RXNO_0000313 hetero-Diels-Alder reaction A Diels-Alder reaction between a diene and an imine or an azadiene and an alkene to give a six-membered nitrogen-containing ring compound. http://purl.obolibrary.org/obo/RXNO_0000093 extrusion reaction http://purl.obolibrary.org/obo/RXNO_0000073 cleaving reaction A cleaving reaction in which a skeletal atom or group of atoms is removed from the middle of a molecule. http://purl.obolibrary.org/obo/RXNO_0000094 Ramberg-Bäcklund reaction http://purl.obolibrary.org/obo/RXNO_0000093 extrusion reaction The reaction of an alpha-halosulfone to give an alkene, with the extrusion of sulfur dioxide. http://purl.obolibrary.org/obo/RXNO_0000096 azo coupling http://purl.obolibrary.org/obo/RXNO_0000011 functional group modification A coupling reaction of a diazonium salt with a phenol or aniline to give an azo compound. http://purl.obolibrary.org/obo/RXNO_0000097 imino-Reformatsky reaction http://purl.obolibrary.org/obo/RXNO_0000036 Reformatsky reaction A carbon-carbon coupling reaction where an imine reacts with a alpha-halo ester and zinc to form a beta-amino ester. http://purl.obolibrary.org/obo/RXNO_0000098 Glaser coupling http://purl.obolibrary.org/obo/RXNO_0000039 carbon-carbon homocoupling reaction A coupling reaction between two molecules of a terminal alkyne catalysed by Cu(I) salts. http://purl.obolibrary.org/obo/RXNO_0000099 Eglinton reaction http://purl.obolibrary.org/obo/RXNO_0000039 carbon-carbon homocoupling reaction A coupling reaction between two molecules of a terminal alkyne using stoichiometric Cu(II) salts. http://purl.obolibrary.org/obo/RXNO_0000100 Cadiot-Chodkiewicz coupling http://purl.obolibrary.org/obo/RXNO_0000000 molecular skeleton joining reaction A coupling reaction between a terminal alkyne and an alkynyl halide catalysed by Cu(I) salts. http://purl.obolibrary.org/obo/RXNO_0000101 Leuckart reaction http://purl.obolibrary.org/obo/RXNO_0000335 reductive amination The reductive amination of ketones or aldehydes with an ammonium formate or formamide to form an amine. http://purl.obolibrary.org/obo/RXNO_0000102 Leuckart-Wallach reaction http://purl.obolibrary.org/obo/RXNO_0000335 reductive amination The reductive amination of ketones or aldehydes with an amine and formic acid to form amines. http://purl.obolibrary.org/obo/RXNO_0000103 Gabriel synthesis http://purl.obolibrary.org/obo/RXNO_0000331 substitution step The reaction of primary alkyl halides with sodium or potassium phthalimide, followed by hydrolysis, to give the corresponding primary amine. http://purl.obolibrary.org/obo/RXNO_0000104 Ing-Manske procedure http://purl.obolibrary.org/obo/RXNO_0000331 substitution step The reaction of primary alkyl halides with sodium or potassium phthalimide, followed by treatment with hydrazine, to give the corresponding primary amine. http://purl.obolibrary.org/obo/RXNO_0000105 end-of-chain chain shortening http://purl.obolibrary.org/obo/RXNO_0000073 cleaving reaction A reaction in which a single skeletal atom is removed from the end of a chain. http://purl.obolibrary.org/obo/RXNO_0000106 Hunsdiecker reaction http://purl.obolibrary.org/obo/RXNO_0000105 end-of-chain chain shortening The decarboxylation of silver carboxylates with halogens to give organic halides. http://purl.obolibrary.org/obo/RXNO_0000107 malonic ester synthesis http://purl.obolibrary.org/obo/RXNO_0000000 molecular skeleton joining reaction A carbon-carbon coupling reaction between a dialkyl malonate and an alkyl halide, to give a substituted acetic acid. The base/R'X treatment can be repeated to give a disubstituted product. http://purl.obolibrary.org/obo/RXNO_0000108 ring expansion http://purl.obolibrary.org/obo/RXNO_0000005 ring formation reaction step A reaction in which an existing ring is increased in size. http://purl.obolibrary.org/obo/RXNO_0000109 Pfitzinger reaction http://purl.obolibrary.org/obo/RXNO_0000108 ring expansion The reaction between isatin and an alpha-methylene carbonyl compound to give a substituted quinoline-4-carboxylic acid. http://purl.obolibrary.org/obo/RXNO_0000110 fragmentation reaction http://purl.obolibrary.org/obo/RXNO_0000073 cleaving reaction A reaction in which the parent molecule breaks up into three or more products. http://purl.obolibrary.org/obo/RXNO_0000111 Grob fragmentation http://purl.obolibrary.org/obo/RXNO_0000110 fragmentation reaction The fragmentation of a molecule that takes place when an electron-donating fragment (X) and an electron-accepting fragment (X') are situated at positions 1 and 3 on an aliphatic chain, to give a cationic fragment, a neutral fragment (e.g. an alkene) and an anionic fragment. http://purl.obolibrary.org/obo/RXNO_0000113 Brook rearrangement http://purl.obolibrary.org/obo/RXNO_0000025 rearrangement step The rearrangement of an alpha-, beta- or gamma-hydroxy silane to give a silyl ether. It is catalysed by a base. http://purl.obolibrary.org/obo/RXNO_0000114 Nicholas reaction http://purl.obolibrary.org/obo/RXNO_0000331 substitution step The reaction of a propargylic cation (stabilised with dicobalt octacarbonyl) with a nucleophile to give a substituted alkyne. http://purl.obolibrary.org/obo/RXNO_0000115 Nicholas reaction, nucleophilic heteroatom centre http://purl.obolibrary.org/obo/RXNO_0000114 Nicholas reaction The reaction of a propargylic cation (stabilised with dicobalt octacarbonyl) with a hydride or amine or enamine to give a substituted alkyne. http://purl.obolibrary.org/obo/RXNO_0000116 Nicholas reaction, nucleophilic carbon centre http://purl.obolibrary.org/obo/RXNO_0000114 Nicholas reaction The reaction of a propargylic cation (stabilised with dicobalt octacarbonyl) with a nucleophilic carbon centre (on e.g. enolates, allyl silanes, ketones, electron-rich aromatics, beta-dicarbonyl compounds) to give a substituted alkyne. http://purl.obolibrary.org/obo/RXNO_0000117 Julia olefination http://purl.obolibrary.org/obo/RXNO_0000479 olefination A carbon-carbon coupling reaction between a phenyl sulfone and an aldehyde or ketone to give a (typically trans) alkene. http://purl.obolibrary.org/obo/RXNO_0000118 Sommelet reaction http://purl.obolibrary.org/obo/RXNO_0000011 functional group modification The oxidation of a benzylic halide to give an aldehyde. The reaction uses hexamethylenetetramine. http://purl.obolibrary.org/obo/RXNO_0000119 Bouveault-Blanc reaction http://purl.obolibrary.org/obo/RXNO_0000037 functional group reduction The reduction of an ester using sodium to give two alcohols. http://purl.obolibrary.org/obo/RXNO_0000120 Payne rearrangement http://purl.obolibrary.org/obo/RXNO_0000202 ring rearrangement A base-catalysed isomerisation of a 2,3-epoxyalcohol, with inversion of configuration at C2. http://purl.obolibrary.org/obo/RXNO_0000121 aza-Payne rearrangement http://purl.obolibrary.org/obo/RXNO_0000202 ring rearrangement A base-catalysed isomerisation of a 2,3-epoxyamine to form a hydroxy aziridine, with inversion of configuration at C2. http://purl.obolibrary.org/obo/RXNO_0000122 Baker-Venkataraman rearrangement http://purl.obolibrary.org/obo/RXNO_0000025 rearrangement step The base-catalysed rearrangement of an o-acetoxyacetophenone to give a hydroxyphenyl-1,3-diketone. http://purl.obolibrary.org/obo/RXNO_0000123 molecular skeleton elimination reaction http://purl.obolibrary.org/obo/RXNO_0000010 functional modification A reaction in which two or more groups of atoms are removed from the molecule, resulting in a change of skeletal bond order. http://purl.obolibrary.org/obo/RXNO_0000124 Bamford-Stevens reaction http://purl.obolibrary.org/obo/RXNO_0000123 molecular skeleton elimination reaction The reaction of a tosylhydrazone of an aldehyde or ketone with a strong base to give an olefin. http://purl.obolibrary.org/obo/RXNO_0000125 Shapiro reaction http://purl.obolibrary.org/obo/RXNO_0000123 molecular skeleton elimination reaction The reaction of a tosylhydrazone of an aldehyde or ketone with an alkyllithium or Grignard reagent to give an olefin. http://purl.obolibrary.org/obo/RXNO_0000126 Doebner reaction http://purl.obolibrary.org/obo/RXNO_0000393 quinoline synthesis The reaction between an aromatic amine, an aldehyde and pyruvic acid on heating to give a quinoline 4-carboxylic acid (cinchoninic acid). http://purl.obolibrary.org/obo/RXNO_0000127 Balz-Schiemann reaction http://purl.obolibrary.org/obo/RXNO_0000332 aromatic substitution step The conversion of an aromatic amine to the corresponding fluoride via the diazonium fluoroborate. http://purl.obolibrary.org/obo/RXNO_0000128 Kolbe electrolysis http://purl.obolibrary.org/obo/RXNO_0000002 carbon-carbon coupling reaction The decarboxylation and coupling of a carboxylate or mixture of carboxylates to give a dimer. http://purl.obolibrary.org/obo/RXNO_0000129 Ugi reaction http://purl.obolibrary.org/obo/MOP_0000628 molecular dehydration reaction Reaction of a ketone or aldehyde, amine, an isocyanide and carboxylic acid to form a bisamide. http://purl.obolibrary.org/obo/RXNO_0000130 Wacker-Tsuji oxidation http://purl.obolibrary.org/obo/RXNO_0000012 functional group oxidation The oxidation of a terminal alkene or ethene to a methyl ketone or acetaldehyde, catalysed by PdCl2 and CuCl2, and using molecular oxygen as the oxidant. http://purl.obolibrary.org/obo/RXNO_0000131 Wacker process http://purl.obolibrary.org/obo/RXNO_0000130 Wacker-Tsuji oxidation The oxidation of ethene to acetaldehyde, catalysed by PdCl2 and CuCl2, and using molecular oxygen as the oxidant. http://purl.obolibrary.org/obo/RXNO_0000132 Monsanto process http://purl.obolibrary.org/obo/RXNO_0000000 molecular skeleton joining reaction The reaction of carbon monoxide with methanol to form acetic acid, catalysed by a rhodium complex. http://purl.obolibrary.org/obo/RXNO_0000133 Cativa process http://purl.obolibrary.org/obo/RXNO_0000000 molecular skeleton joining reaction The reaction of carbon monoxide with methanol to form acetic acid, catalysed by an iridium complex. http://purl.obolibrary.org/obo/RXNO_0000134 Barton-McCombie deoxygenation http://purl.obolibrary.org/obo/RXNO_0000037 functional group reduction The deoxygenation of an alcohol to the corresponding alkane using a thiochloroformate. It proceeds by a radical mechanism. http://purl.obolibrary.org/obo/RXNO_0000135 Barton decarboxylation http://purl.obolibrary.org/obo/RXNO_0000105 end-of-chain chain shortening The decarboxylation of a carboxylic acid to the lower homologue alkane using a pyridine thione. http://purl.obolibrary.org/obo/RXNO_0000136 Rosenmund reduction http://purl.obolibrary.org/obo/RXNO_0000037 functional group reduction The hydrogenolysis of an acyl halide to the corresponding aldehyde, catalysed by palladium-on-barium sulfate. http://purl.obolibrary.org/obo/RXNO_0000137 Sonogashira coupling http://purl.obolibrary.org/obo/RXNO_0000316 palladium-catalysed carbon-carbon coupling reaction A carbon-carbon coupling reaction where a terminal alkyne reacts with an aryl halide to give an aryl alkyne. It is catalysed by palladium. http://purl.obolibrary.org/obo/RXNO_0000138 benzoin condensation http://purl.obolibrary.org/obo/RXNO_0000000 molecular skeleton joining reaction A reaction between two aromatic aldehydes to give a benzoin (an alpha-hydroxyketone). http://purl.obolibrary.org/obo/RXNO_0000139 Gattermann reaction http://purl.obolibrary.org/obo/MOP_0000003 formylation The formylation of an arene with hydrogen cyanide to give an aryl aldehyde or ketone. http://purl.obolibrary.org/obo/RXNO_0000140 Suzuki-Miyaura coupling http://purl.obolibrary.org/obo/RXNO_0000592 Suzuki-type coupling The coupling of a boronic acid or boronic ester with an unsaturated halide, triflate or sulfonate catalysed by a palladium(0) complex. http://purl.obolibrary.org/obo/RXNO_0000141 Sharpless asymmetric epoxidation http://purl.obolibrary.org/obo/MOP_0000671 epoxidation The epoxidation of an allylic alcohol to give a beta,gamma-epoxy alcohol, with control of absolute stereochemistry at the two new stereocentres. The oxidising agent is tert-butyl hydroperoxide, and the catalyst is a complex of titanium salt and optically active diethyl tartrate. http://purl.obolibrary.org/obo/RXNO_0000142 Sharpless asymmetric dihydroxylation http://purl.obolibrary.org/obo/RXNO_0000041 addition reaction step The dihydroxylation of an alkene to give an alpha,beta-diol, with control of absolute stereochemistry at the two new stereocentres. The oxidising agent is osmium tetroxide, which is used catalytically with a stoichiometric oxidant and a chiral ligand. The reagents are available commercially as AD-mix. http://purl.obolibrary.org/obo/RXNO_0000143 Sharpless asymmetric aminohydroxylation http://purl.obolibrary.org/obo/RXNO_0000041 addition reaction step The aminohydroxylation of an alkene to give a beta-amino alcohol, with control of absolute stereochemistry at the two new stereocentres. The oxidising agent is an oxygen-containing osmium species and/or an amino derivative which can be used catalytically with a stoichiometric oxidant and a chiral ligand. http://purl.obolibrary.org/obo/RXNO_0000144 Kumada coupling http://purl.obolibrary.org/obo/RXNO_0000002 carbon-carbon coupling reaction A cross-coupling reaction between a Grignard reagent and an activated (aryl or vinyl) halide or triflate. The reaction is catalysed by a palladium or nickel catalyst. http://purl.obolibrary.org/obo/RXNO_0000145 Barbier-Wieland degradation http://purl.obolibrary.org/obo/RXNO_0000105 end-of-chain chain shortening The degradation of a carboxylic acid to its next lower homologous carboxylic acid. http://purl.obolibrary.org/obo/RXNO_0000146 Corey-Fuchs reaction http://purl.obolibrary.org/obo/RXNO_0000070 chain lengthening A homologation reaction of an aldehyde to yield a terminal alkyne. The reagents are tetrabromomethane, triphenylphosphine, butyllithium and water. http://purl.obolibrary.org/obo/RXNO_0000147 Emde degradation http://purl.obolibrary.org/obo/RXNO_0000073 cleaving reaction A reduction of a quaternary ammonium salt containing at least one unsaturated substituent, to give a tertiary amine. http://purl.obolibrary.org/obo/RXNO_0000148 Claisen rearrangement http://purl.obolibrary.org/obo/MOP_0000721 [3,3]-sigmatropic rearrangement The [3,3]-sigmatropic rearrangement of an allyl vinyl ether to give a gamma,delta-unsaturated carbonyl compound. http://purl.obolibrary.org/obo/RXNO_0000149 Ireland-Claisen rearrangement http://purl.obolibrary.org/obo/MOP_0000721 [3,3]-sigmatropic rearrangement The enolisation and subsequent [3,3]-sigmatropic rearrangement of an allylic acetate to give a gamma,delta-unsaturated carboxylic acid. http://purl.obolibrary.org/obo/RXNO_0000150 joining with rearrangement http://purl.obolibrary.org/obo/RXNO_0000000 molecular skeleton joining reaction A reaction in which one or more atoms are added to the molecular skeleton and a skeletal rearrangement occurs. http://purl.obolibrary.org/obo/RXNO_0000151 Bellus-Claisen rearrangement http://purl.obolibrary.org/obo/MOP_0000721 [3,3]-sigmatropic rearrangement The coupling and subsequent [3,3]-sigmatropic rearrangement of an allylic ether or allylic thioether or allylic amine and a ketene to give the corresponding gamma,delta-unsaturated carbonyl compound. http://purl.obolibrary.org/obo/RXNO_0000152 Eschenmoser-Claisen rearrangement http://purl.obolibrary.org/obo/MOP_0000721 [3,3]-sigmatropic rearrangement The coupling and subsequent [3,3]-sigmatropic rearrangement of an allylic alcohol and alpha,alpha-dialkoxy ethylamine to give a gamma,delta-unsaturated dialkyl amide. http://purl.obolibrary.org/obo/RXNO_0000153 Johnson-Claisen rearrangement http://purl.obolibrary.org/obo/MOP_0000721 [3,3]-sigmatropic rearrangement The coupling and subsequent [3,3]-sigmatropic rearrangement of an allylic alcohol and trimethyl orthoacetate to give a gamma,delta-unsaturated alkyl ester. http://purl.obolibrary.org/obo/RXNO_0000154 Swern oxidation http://purl.obolibrary.org/obo/MOP_0000572 alcohol oxidation The oxidation of a primary alcohol or secondary alcohol to an aldehyde or ketone respectively. Does not work with allylic or benzylic alcohols. http://purl.obolibrary.org/obo/RXNO_0000155 Finkelstein reaction http://purl.obolibrary.org/obo/RXNO_0000011 functional group modification The conversion of an alkyl chloride, alkyl bromide or alkyl sulfonate ester to an alkyl iodide by SN2 substitution. The reaction relies upon the equilibrium being pushed to completion by the precipitation. http://purl.obolibrary.org/obo/RXNO_0000156 Lossen rearrangement http://purl.obolibrary.org/obo/RXNO_0000025 rearrangement step The derivatisation (for example with tosyl chloride) and subsequent rearrangement of a hydroxamic acid to give an isocyanate. http://purl.obolibrary.org/obo/RXNO_0000157 Nef reaction http://purl.obolibrary.org/obo/RXNO_0000011 functional group modification The conversion of a primary nitroalkane or secondary nitroalkane to an aldehyde or ketone, respectively. http://purl.obolibrary.org/obo/RXNO_0000158 Japp-Klingemann reaction http://purl.obolibrary.org/obo/RXNO_0000073 cleaving reaction The reaction of a doubly activated methylene compound that has at least one carbonyl substituent with an aryl azide to give a hydrazone. Usually there is concomitant cleaving and oxidation of one of the carbonyl substituents. http://purl.obolibrary.org/obo/RXNO_0000159 Doebner-Miller reaction http://purl.obolibrary.org/obo/RXNO_0000052 fused-ring-system formation The formation of a quinoline from a primary aromatic amine and an alpha,beta-unsaturated carbonyl compound. http://purl.obolibrary.org/obo/RXNO_0000160 Fmoc protection http://purl.obolibrary.org/obo/RXNO_0000321 amino group protection The protection of an amine (often a peptide) as its 9H-fluoren-9-ylmethoxycarbonyl derivative. http://purl.obolibrary.org/obo/RXNO_0000161 Paal-Knorr synthesis http://purl.obolibrary.org/obo/RXNO_0000005 ring formation reaction step The cyclisation of a 1,4-dicarbonyl compound with another molecule to give a five-membered aromatic ring compound. http://purl.obolibrary.org/obo/RXNO_0000162 Paal-Knorr furan synthesis http://purl.obolibrary.org/obo/RXNO_0000346 oxacycle synthesis The cyclisation of a 1,4-dicarbonyl compound with an acid catalyst to give a furan. http://purl.obolibrary.org/obo/RXNO_0000163 Paal-Knorr thiophene synthesis http://purl.obolibrary.org/obo/RXNO_0000348 thiacycle synthesis The cyclisation of a 1,4-dicarbonyl compound with phosphorus pentasulfide to give a thiophene. http://purl.obolibrary.org/obo/RXNO_0000164 Paal-Knorr pyrrole synthesis http://purl.obolibrary.org/obo/RXNO_0000497 pyrrole synthesis The cyclisation of a 1,4-dicarbonyl compound with an amine to give a pyrrole. http://purl.obolibrary.org/obo/RXNO_0000165 Schotten-Baumann reaction http://purl.obolibrary.org/obo/RXNO_0000331 substitution step The coupling of an alcohol or amine with an acyl chloride to give an ester or amide. A two-phase solvent system is often used, to enable the acid generated during the reaction to be neutralised by the aqueous base, while the starting materials and products remain in the organic phase. http://purl.obolibrary.org/obo/RXNO_0000166 Hofmann elimination http://purl.obolibrary.org/obo/RXNO_0000123 molecular skeleton elimination reaction The elimination of a methylated amine from an alkylamine to form an olefin. The reaction proceeds via the quaternary ammonium salt. http://purl.obolibrary.org/obo/RXNO_0000167 Fischer-Speier esterification http://purl.obolibrary.org/obo/RXNO_0000331 substitution step The esterification of a carboxylic acid with an alcohol. Various Lewis acids or Bronsted acids may be used as catalyst. http://purl.obolibrary.org/obo/RXNO_0000168 Weerman reaction http://purl.obolibrary.org/obo/RXNO_0000105 end-of-chain chain shortening The degradation of an alpha-hydroxy amide or an alpha,beta-unsaturated amide to the lower homologue aldehyde, especially in carbohydrate chemistry. The process proceeds via Hofmann degradation. http://purl.obolibrary.org/obo/RXNO_0000169 Dakin reaction http://purl.obolibrary.org/obo/RXNO_0000073 cleaving reaction The reaction of ortho- or para-phenolic (or ortho- or para-anilinic) aldehydes or ketones with hydrogen peroxide to form bisphenols (or hydroxy anilines) and carboxylic acids. http://purl.obolibrary.org/obo/RXNO_0000170 Schmidt rearrangement, carboxylic acid http://purl.obolibrary.org/obo/RXNO_0000105 end-of-chain chain shortening The reaction of a carboxylic acid with hydrazoic acid to give the lower homologue amine, with the loss of the terminal carbon atom. http://purl.obolibrary.org/obo/RXNO_0000171 Schmidt rearrangement, ketone http://purl.obolibrary.org/obo/RXNO_0000030 molecular skeleton insertion reaction The reaction of a ketone with hydrazoic acid with the insertion of an NH group between the carbonyl carbon and one of the R groups to form an amide. http://purl.obolibrary.org/obo/RXNO_0000172 Schmidt rearrangement, tertiary alcohol http://purl.obolibrary.org/obo/RXNO_0000030 molecular skeleton insertion reaction The reaction of a tertiary alcohol with hydrazoic acid with rearrangement to form an imide. http://purl.obolibrary.org/obo/RXNO_0000173 Schmidt rearrangement, alkene http://purl.obolibrary.org/obo/RXNO_0000030 molecular skeleton insertion reaction The reaction of an alkene with hydrazoic acid with rearrangement to form an imide. http://purl.obolibrary.org/obo/RXNO_0000174 Sommelet-Hauser rearrangement http://purl.obolibrary.org/obo/RXNO_0000025 rearrangement step The [2,3]-sigmatropic rearrangement of a benzyl quaternary ammonium salt to form an aniline. http://purl.obolibrary.org/obo/RXNO_0000175 Dakin-West reaction http://purl.obolibrary.org/obo/RXNO_0000000 molecular skeleton joining reaction The reaction of an amino acid with an acid anhydride to give an alpha-acylamido ketone. The reaction proceeds via the mixed anhydride and an oxazolone; the product is always racemic. http://purl.obolibrary.org/obo/RXNO_0000176 Beckmann fragmentation http://purl.obolibrary.org/obo/RXNO_0000073 cleaving reaction The cleavage of an oxime to the corresponding nitrile and an alkyl halide. This reaction is related to the Beckmann rearrangement, and occurs when the R group that is anti to the oxime hydroxyl is quaternary. http://purl.obolibrary.org/obo/RXNO_0000177 Kharasch reaction http://purl.obolibrary.org/obo/RXNO_0000070 chain lengthening The transfer of a hydrogen or halogen atom from a haloalkane to an alkene, giving the chain-extended halogenated alkane. http://purl.obolibrary.org/obo/RXNO_0000178 Kharasch-Sosnovsky reaction http://purl.obolibrary.org/obo/RXNO_0000331 substitution step The allylic oxidation of an alkene with a peroxy ester or a peroxide to give the corresponding allylic alcohol derivative. The catalyst is a copper compound. http://purl.obolibrary.org/obo/RXNO_0000179 Elbs persulfate oxidation, phenol variant http://purl.obolibrary.org/obo/RXNO_0000332 aromatic substitution step The oxidation of a phenol to give a (predominantly para) diphenol using potassium persulfate. http://purl.obolibrary.org/obo/RXNO_0000180 Elbs persulfate oxidation, tolyl variant http://purl.obolibrary.org/obo/RXNO_0000012 functional group oxidation The oxidation of a methyl-substituted aromatic compound to the corresponding benzaldehyde using potassium persulfate. http://purl.obolibrary.org/obo/RXNO_0000181 Boyland-Sims oxidation http://purl.obolibrary.org/obo/RXNO_0000332 aromatic substitution step The oxidation of an aromatic amine to give a (predominantly ortho) amino aryl sulfate using potassium persulfate followed by hydrolysis to yield the corresponding aminophenol. http://purl.obolibrary.org/obo/RXNO_0000182 Kolbe-Schmitt reaction http://purl.obolibrary.org/obo/MOP_0000713 carboxylation The (predominantly ortho) carboxylation of a phenoxide. http://purl.obolibrary.org/obo/RXNO_0000183 Perkow reaction http://purl.obolibrary.org/obo/RXNO_0000000 molecular skeleton joining reaction The reaction between an alpha-halocarbonyl compound and a trialkyl phosphite to give an enol phosphate. http://purl.obolibrary.org/obo/RXNO_0000184 Pfitzner-Moffatt oxidation http://purl.obolibrary.org/obo/RXNO_0000012 functional group oxidation The oxidation of a primary or secondary alcohol to the corresponding aldehyde or ketone respectively using dimethyl sulfoxide, 1,3-dicyclohexylcarbodiimide and acid. The reaction proceeds via an alkoxysulfonium ylide. http://purl.obolibrary.org/obo/RXNO_0000185 Willgerodt reaction http://purl.obolibrary.org/obo/RXNO_0000011 functional group modification The conversion of an aryl alkyl ketone to an amide and/or an ammonium salt of a carboxylic acid using ammonium polysulfide. The carbonyl group of the product is always at the end of the alkyl chain. http://purl.obolibrary.org/obo/RXNO_0000186 Willgerodt-Kindler reaction http://purl.obolibrary.org/obo/RXNO_0000011 functional group modification The conversion of an aryl alkyl ketone to an amide using sulfur and dry ammonia or a primary or secondary amine. The amide carbonyl group is always at the end of the alkyl chain. http://purl.obolibrary.org/obo/RXNO_0000187 Tishchenko reaction http://purl.obolibrary.org/obo/RXNO_0000011 functional group modification The formation of an ester from two aldehydes via a disproportionation process using a metal alkoxide to oxidise one aldehyde and reduce the other. http://purl.obolibrary.org/obo/RXNO_0000188 Zimmermann reaction http://purl.obolibrary.org/obo/RXNO_0000002 carbon-carbon coupling reaction The reaction between a methylene ketone and a polynitro aromatic compound. http://purl.obolibrary.org/obo/RXNO_0000189 Neber rearrangement http://purl.obolibrary.org/obo/RXNO_0000025 rearrangement step The rearrangement of the sulfonic ester of a ketoxime in base to give an alpha-amino ketone. http://purl.obolibrary.org/obo/RXNO_0000191 Nozaki-Hiyama-Kishi reaction http://purl.obolibrary.org/obo/RXNO_0000000 molecular skeleton joining reaction A coupling reaction of an aldehyde to an allyl, vinyl or aryl halide or triflate in the presence of chromium(II). It is catalysed by nickel. http://purl.obolibrary.org/obo/RXNO_0000192 Buchwald-Hartwig amination http://purl.obolibrary.org/obo/RXNO_0000332 aromatic substitution step A reaction in which an aryl halide or aryl triflate reacts with a primary or secondary amine in the presence of base to give a secondary or tertiary amine. It is catalysed by a palladium catalyst. http://purl.obolibrary.org/obo/RXNO_0000193 Hiyama coupling http://purl.obolibrary.org/obo/RXNO_0000002 carbon-carbon coupling reaction A carbon-carbon coupling reaction where an organosilane reacts with an organic halide or triflate. It is catalysed by a palladium or nickel complex. http://purl.obolibrary.org/obo/RXNO_0000194 Stevens rearrangement http://purl.obolibrary.org/obo/RXNO_0000025 rearrangement step The 1,2-rearrangement of an alpha-methylene ammonium salt or alpha-methylene sulfonium salt to an amine or sulfide in the presence of strong base. http://purl.obolibrary.org/obo/RXNO_0000195 Stevens rearrangement, ammonium http://purl.obolibrary.org/obo/RXNO_0000194 Stevens rearrangement The 1,2-rearrangement of an alpha-methylene ammonium salt to an amine in the presence of strong base. http://purl.obolibrary.org/obo/RXNO_0000196 Stevens rearrangement, sulfonium http://purl.obolibrary.org/obo/RXNO_0000194 Stevens rearrangement The 1,2-rearrangement of an alpha-methylene sulfonium salt to a sulfide in the presence of strong base. http://purl.obolibrary.org/obo/RXNO_0000197 aza-Cope rearrangement http://purl.obolibrary.org/obo/MOP_0000721 [3,3]-sigmatropic rearrangement A [3,3]-sigmatropic rearrangement where an aza-1,5-hexadiene rearranges to form an aza-1,5-hexadiene. http://purl.obolibrary.org/obo/RXNO_0000198 2-aza-Cope rearrangement http://purl.obolibrary.org/obo/RXNO_0000197 aza-Cope rearrangement The rearrangement of a 2-aza-1,5-hexadiene to form an imine. http://purl.obolibrary.org/obo/RXNO_0000199 3-aza-Cope rearrangement http://purl.obolibrary.org/obo/RXNO_0000197 aza-Cope rearrangement The rearrangement of a 3-aza-1,5-hexadiene to form a delta,epsilon-unsaturated imine. http://purl.obolibrary.org/obo/RXNO_0000200 1-aza-Cope rearrangement http://purl.obolibrary.org/obo/RXNO_0000197 aza-Cope rearrangement The rearrangement of a delta,epsilon-unsaturated imine to form a 3-aza-1,5-hexadiene. http://purl.obolibrary.org/obo/RXNO_0000201 Steglich rearrangement http://purl.obolibrary.org/obo/RXNO_0000025 rearrangement step The rearrangement of an oxazolyl carbonate to a C-carboxyazlactone. http://purl.obolibrary.org/obo/RXNO_0000202 ring rearrangement http://purl.obolibrary.org/obo/RXNO_0000005 ring formation reaction step A reaction in which the number of rings in a molecule stays the same but the connectivity of the atoms in at least one ring changes. http://purl.obolibrary.org/obo/RXNO_0000203 deprotection reaction http://purl.obolibrary.org/obo/RXNO_0000010 functional modification A reaction in which a protecting group is modified by converting it into a functional group. http://purl.obolibrary.org/obo/RXNO_0000204 multiple-bond metathesis http://purl.obolibrary.org/obo/RXNO_0000000 molecular skeleton joining reaction A joining reaction in which two carbon-carbon multiple bonds are redistributed among two fragments. The reaction is typically catalysed by a metal carbenoid, and proceeds via two four-membered intermediates (metallacyclobutanes). The reaction is driven by release of a low-MW alkene. http://purl.obolibrary.org/obo/RXNO_0000205 ring breaking http://purl.obolibrary.org/obo/RXNO_0000001 planned reaction step A planned reaction step in which the product has fewer rings than the reactants. http://purl.obolibrary.org/obo/RXNO_0000206 ring contraction http://purl.obolibrary.org/obo/RXNO_0000005 ring formation reaction step A planned reaction step in which an existing ring is reduced in size. http://purl.obolibrary.org/obo/RXNO_0000207 Strecker reaction http://purl.obolibrary.org/obo/RXNO_0000070 chain lengthening An addition reaction between a carbonyl compound, an inorganic cyanide and an ammonium salt, followed by hydrolysis, to give an alpha-amino carboxylic acid. http://purl.obolibrary.org/obo/RXNO_0000208 aromatic Claisen rearrangement http://purl.obolibrary.org/obo/MOP_0000721 [3,3]-sigmatropic rearrangement The [3,3]-sigmatropic rearrangement, and subsequent re-aromatisation, of an allyl aryl ether to give an ortho-allyl phenol. http://purl.obolibrary.org/obo/RXNO_0000209 Nazarov cyclisation http://purl.obolibrary.org/obo/RXNO_0000005 ring formation reaction step The acid-catalysed cyclisation of a divinylketone to give a cyclopentenone. http://purl.obolibrary.org/obo/RXNO_0000210 Fleming-Tamao oxidation http://purl.obolibrary.org/obo/RXNO_0000331 substitution step The stereospecific oxidation of a (phenyldimethylsilyl)alkane to the corresponding alcohol using bromine, usually generated in situ from potassium bromide and peracetic acid. http://purl.obolibrary.org/obo/RXNO_0000211 Tamao oxidation http://purl.obolibrary.org/obo/RXNO_0000331 substitution step The stereospecific oxidation of a (halosilyl)alkane to the corresponding alcohol using potassium fluoride and hydrogen peroxide. http://purl.obolibrary.org/obo/RXNO_0000212 Sakurai reaction, aldehyde or ketone http://purl.obolibrary.org/obo/RXNO_0000443 Sakurai reaction A carbon-carbon coupling reaction in which an aldehyde or ketone reacts with allyltrimethylsilane to form a homoallylic alcohol. http://purl.obolibrary.org/obo/RXNO_0000213 Sakurai reaction, enone http://purl.obolibrary.org/obo/RXNO_0000443 Sakurai reaction A carbon-carbon coupling reaction in which an enone reacts with allyltrimethylsilane to form a delta,epsilon-unsaturated carbonyl compound. http://purl.obolibrary.org/obo/RXNO_0000214 Sakurai reaction, acid chloride http://purl.obolibrary.org/obo/RXNO_0000443 Sakurai reaction A carbon-carbon coupling reaction in which an acid chloride reacts with allyltrimethylsilane to form a gamma,delta-unsaturated ketone. http://purl.obolibrary.org/obo/RXNO_0000215 Sakurai reaction, acetal or ketal http://purl.obolibrary.org/obo/RXNO_0000443 Sakurai reaction A carbon-carbon coupling reaction in which an acetal or ketal reacts with allyltrimethylsilane to form a homoallylic ether. http://purl.obolibrary.org/obo/RXNO_0000216 imine Sakurai reaction http://purl.obolibrary.org/obo/RXNO_0000443 Sakurai reaction A carbon-carbon coupling reaction in which an imine reacts with allyltrimethylsilane to form a homoallylic amine. http://purl.obolibrary.org/obo/RXNO_0000217 Sakurai reaction, epoxide http://purl.obolibrary.org/obo/RXNO_0000443 Sakurai reaction A ring-breaking reaction in which an epoxide reacts with allyltrimethylsilane to form a hydroxy alkene. http://purl.obolibrary.org/obo/RXNO_0000218 Cannizzaro reaction http://purl.obolibrary.org/obo/RXNO_0000011 functional group modification The disproportionation of a non-enolisable aldehyde to the corresponding carboxylic acid and alcohol. The reaction is base-catalysed. http://purl.obolibrary.org/obo/RXNO_0000219 crossed Cannizzaro reaction http://purl.obolibrary.org/obo/RXNO_0000011 functional group modification The reaction between two different non-enolisable aldehydes to give a carboxylic acid and an alcohol. The reaction is base-catalysed. http://purl.obolibrary.org/obo/RXNO_0000220 Pummerer rearrangement http://purl.obolibrary.org/obo/RXNO_0000011 functional group modification The conversion of a sulfoxide with an alpha-hydrogen to an alpha-substituted thioether. The reaction is usually performed with an acid anhydride or acyl halide. http://purl.obolibrary.org/obo/RXNO_0000221 Polonovski reaction http://purl.obolibrary.org/obo/RXNO_0000073 cleaving reaction The reaction of a tertiary amine oxide with an anhydride or acyl chloride to give an N,N-disubstituted acetamide and an aldehyde. http://purl.obolibrary.org/obo/RXNO_0000222 Polonovski-Potier reaction http://purl.obolibrary.org/obo/RXNO_0000221 Polonovski reaction The reaction of a tertiary amine oxide with trifluoroacetic anhydride to give an N,N-disubstituted acetamide and an aldehyde. http://purl.obolibrary.org/obo/RXNO_0000223 Menshutkin reaction http://purl.obolibrary.org/obo/MOP_0002369 N-alkylation The alkylation of a tertiary amine with an alkyl halide to the corresponding ammonium salt. http://purl.obolibrary.org/obo/RXNO_0000224 Strecker degradation http://purl.obolibrary.org/obo/RXNO_0000105 end-of-chain chain shortening The deamination and decarboxylation of amino acids to imines and then to aldehydes or ketones, in the presence of a carbonyl compound (especially an alpha,beta-dicarbonyl compound or a reducing sugar such as glucose). The reaction is involved in the generation of meat aromas/flavours in cooking. http://purl.obolibrary.org/obo/RXNO_0000225 Wohl-Ziegler bromination http://purl.obolibrary.org/obo/RXNO_0000373 functional group addition step The allylic or benzylic bromination of hydrocarbons using an N-bromoimide and a radical initiator, to give an allylic or benzylic bromide. http://purl.obolibrary.org/obo/RXNO_0000226 Wolff-Kishner reduction http://purl.obolibrary.org/obo/RXNO_0000037 functional group reduction The reduction of an aldehyde or ketone to the corresponding methylene compound, using hydrazine hydrate and a base. http://purl.obolibrary.org/obo/RXNO_0000227 Wolff-Kishner reduction, Huang-Minlon modification http://purl.obolibrary.org/obo/RXNO_0000226 Wolff-Kishner reduction The reduction of an aldehyde or ketone to the corresponding methylene compound, using hydrazine hydrate and a base in refluxing ethylene glycol. http://purl.obolibrary.org/obo/RXNO_0000228 Zemplen transesterification http://purl.obolibrary.org/obo/RXNO_0000037 functional group reduction The reduction of an ester to the corresponding alcohol, using sodium methoxide in dry methanol. http://purl.obolibrary.org/obo/RXNO_0000229 Ferrier rearrangement http://purl.obolibrary.org/obo/RXNO_0000025 rearrangement step The rearrangement of an O-alkenyl acetal to give the corresponding beta-alkoxy carbonyl compound. http://purl.obolibrary.org/obo/RXNO_0000230 aza-Ferrier rearrangement http://purl.obolibrary.org/obo/RXNO_0000025 rearrangement step The rearrangement of an O-alkenyl hemiaminal ether to give the corresponding beta-amino carbonyl compound. http://purl.obolibrary.org/obo/RXNO_0000231 aza-ene reaction http://purl.obolibrary.org/obo/RXNO_0000000 molecular skeleton joining reaction A joining reaction where an N=C system with an allylic hydrogen reacts with a compound containing a multiple bond (an enophile) to form a substituted alkene. http://purl.obolibrary.org/obo/RXNO_0000232 Petasis reaction http://purl.obolibrary.org/obo/RXNO_0000011 functional group modification The alkylation of an amine with a boronic acid and an aldehyde to give a substituted amine. http://purl.obolibrary.org/obo/RXNO_0000233 Achmatowicz rearrangement http://purl.obolibrary.org/obo/RXNO_0000202 ring rearrangement A rearrangement of a furfuryl alcohol derivative to a dihydropyranone, from which monosaccharides may be synthesised. http://purl.obolibrary.org/obo/RXNO_0000234 aza-Achmatowicz rearrangement http://purl.obolibrary.org/obo/RXNO_0000202 ring rearrangement A rearrangement of a furfuryl amine derivative to a tetrahydropyridinone. http://purl.obolibrary.org/obo/RXNO_0000235 aza-Henry reaction http://purl.obolibrary.org/obo/RXNO_0000002 carbon-carbon coupling reaction A carbon-carbon coupling reaction between a nitroalkane and an imine to give a beta-amino nitroalkane. http://purl.obolibrary.org/obo/RXNO_0000236 Biginelli reaction http://purl.obolibrary.org/obo/MOP_0000628 molecular dehydration reaction A three-component coupling of a beta-keto ester, an aldehyde and urea to give a 3,4-dihydropyrimidinone. http://purl.obolibrary.org/obo/RXNO_0000237 Blaise reaction http://purl.obolibrary.org/obo/RXNO_0000002 carbon-carbon coupling reaction The coupling of an alpha-bromo ester with a nitrile to give a beta-ketoester, in the presence of zinc. http://purl.obolibrary.org/obo/RXNO_0000238 Katritzky pyrylium-pyridinium method http://purl.obolibrary.org/obo/RXNO_0000331 substitution step The substitution of an amine with a nucleophile using a pyrylium salt. http://purl.obolibrary.org/obo/RXNO_0000239 metalla-aza-Claisen rearrangement http://purl.obolibrary.org/obo/RXNO_0000025 rearrangement step The rearrangement of a 3-aza-4-metalla-1,5-hexadiene to form a delta,epsilon-unsaturated metallaimine. http://purl.obolibrary.org/obo/RXNO_0000240 Bergman cyclisation http://purl.obolibrary.org/obo/RXNO_0000005 ring formation reaction step The cyclisation of an ene-diyne to give a 1,4-diradical cyclohexatriene. The diradical usually aromatises. http://purl.obolibrary.org/obo/RXNO_0000241 nitro-Michael reaction http://purl.obolibrary.org/obo/RXNO_0000009 Michael addition A conjugate addition reaction where a carbon nucleophile adds to an alpha,beta-unsaturated nitro compound. http://purl.obolibrary.org/obo/RXNO_0000242 Noyori asymmetric hydrogenation, alkene http://purl.obolibrary.org/obo/RXNO_0000041 addition reaction step The homogeneous asymmetric catalytic hydrogenation of a C=C double bond using a ruthenium(II) BINAP catalyst. http://purl.obolibrary.org/obo/RXNO_0000243 Noyori asymmetric hydrogenation, carbonyl http://purl.obolibrary.org/obo/RXNO_0000037 functional group reduction The homogeneous asymmetric catalytic hydrogenation of a carbonyl bond using a ruthenium(II) BINAP catalyst. http://purl.obolibrary.org/obo/RXNO_0000244 Passerini reaction http://purl.obolibrary.org/obo/RXNO_0000000 molecular skeleton joining reaction The reaction between an isonitrile, a carboxylic acid and aldehyde or ketone to give an alpha-acyloxy amide. http://purl.obolibrary.org/obo/RXNO_0000245 ring-closing metathesis http://purl.obolibrary.org/obo/RXNO_0000005 ring formation reaction step A joining reaction in which two carbon-carbon double bonds in the same molecule are redistributed to give a cycloalkene. It is typically catalysed by a metal carbenoid, and proceeds via two four-membered intermediates (metallacyclobutanes). The reaction is driven by release of a low-MW alkene. http://purl.obolibrary.org/obo/RXNO_0000246 polymerisation reaction http://purl.obolibrary.org/obo/RXNO_0000000 molecular skeleton joining reaction A joining reaction, the objective of which is that a large number of monomers react together to produce a polymer consisting of repeating units. http://purl.obolibrary.org/obo/RXNO_0000247 ring-opening metathesis polymerisation http://purl.obolibrary.org/obo/RXNO_0000246 polymerisation reaction A joining reaction in which two carbon-carbon double bonds are redistributed among two fragments, i.e. two alkenes. It is typically catalysed by a metal carbenoid, and proceeds via two four-membered intermediates (metallacyclobutanes). The reaction is driven by release of ring strain in the cycloalkene. http://purl.obolibrary.org/obo/RXNO_0000248 Carroll rearrangement http://purl.obolibrary.org/obo/RXNO_0000025 rearrangement step An adaptation of the Claisen rearrangement that transforms a beta-keto allyl ester into a gamma,delta-allyl ketone. It uses base and high temperature or milder conditions with a ruthenium or palladium complex as catalyst. http://purl.obolibrary.org/obo/RXNO_0000249 Bose-Mitsunobu reaction http://purl.obolibrary.org/obo/RXNO_0000034 Mitsunobu reaction A Mitsunobu reaction, where an alcohol is converted to something else with inversion at the stereocentre, using diphenylphosphoryl azide. http://purl.obolibrary.org/obo/RXNO_0000250 Fritsch-Buttenberg-Wiechell rearrangement http://purl.obolibrary.org/obo/RXNO_0000025 rearrangement step The rearrangement of a 2-bromoalkene into an alkyne, mediated by strong base. http://purl.obolibrary.org/obo/RXNO_0000251 Stork-Wittig olefination http://purl.obolibrary.org/obo/RXNO_0000479 olefination A carbon-carbon coupling reaction where an aldehyde reacts with a phosphonium salt to give a Z-iodoalkene. The reaction is mediated by sodium or potassium hexamethyldisilazide. http://purl.obolibrary.org/obo/RXNO_0000252 Cadogan carbazole synthesis http://purl.obolibrary.org/obo/RXNO_0000521 carbazole synthesis The reduction of a 2-nitrobiaryl compound to give a carbazole. http://purl.obolibrary.org/obo/RXNO_0000253 Cadogan coupling http://purl.obolibrary.org/obo/RXNO_0000002 carbon-carbon coupling reaction The arylation of an arylamine mediated by isopentyl nitrite. http://purl.obolibrary.org/obo/RXNO_0000254 MacDonald condensation http://purl.obolibrary.org/obo/RXNO_0000052 fused-ring-system formation The reaction between a 1,9-diformyldipyrromethane and a dipyrromethane to give a porphodimethene. http://purl.obolibrary.org/obo/RXNO_0000255 Zweifel diene synthesis http://purl.obolibrary.org/obo/RXNO_0000039 carbon-carbon homocoupling reaction The carbon-carbon homocoupling reaction of a pair of alkyne molecules using a borane and iodine. The reaction proceeds via a borane intermediate. http://purl.obolibrary.org/obo/RXNO_0000256 Dess-Martin oxidation http://purl.obolibrary.org/obo/MOP_0000572 alcohol oxidation The oxidation of a primary alcohol to an aldehyde or a secondary alcohol to a ketone using the Dess-Martin periodinane. http://purl.obolibrary.org/obo/RXNO_0000257 Criegee oxidation http://purl.obolibrary.org/obo/RXNO_0000344 alkene oxidative cleavage The oxidative cleavage of an alpha,beta-diol using lead tetraacetate to give the corresponding carbonyl compounds. http://purl.obolibrary.org/obo/RXNO_0000258 Simmons-Smith reaction http://purl.obolibrary.org/obo/RXNO_0000005 ring formation reaction step A ring formation reaction where an alkene reacts with a dihalomethane in the presence of a metal atom or metal complexes to form a cyclopropane. The traditional reaction uses a zinc-copper couple and diiodomethane. http://purl.obolibrary.org/obo/RXNO_0000259 Wittig rearrangement http://purl.obolibrary.org/obo/RXNO_0000025 rearrangement step Any of a family of sigmatropic rearrangements that involve the migration of a group on an electronegative atom (O or N) to a carbon atom. http://purl.obolibrary.org/obo/RXNO_0000260 [1,2]-Wittig rearrangement http://purl.obolibrary.org/obo/RXNO_0000259 Wittig rearrangement A base-mediated 1,2-sigmatropic rearrangement of an ether to give an alcohol. http://purl.obolibrary.org/obo/RXNO_0000261 [2,3]-Wittig rearrangement http://purl.obolibrary.org/obo/RXNO_0000259 Wittig rearrangement A base-mediated 2,3-sigmatropic rearrangement of an allyl ether to give a homoallylic alcohol. http://purl.obolibrary.org/obo/RXNO_0000262 [1,2]-aza-Wittig rearrangement http://purl.obolibrary.org/obo/RXNO_0000259 Wittig rearrangement A base-mediated 1,2-sigmatropic rearrangement of a tertiary amine to give a secondary amine. http://purl.obolibrary.org/obo/RXNO_0000263 [2,3]-aza-Wittig rearrangement http://purl.obolibrary.org/obo/RXNO_0000259 Wittig rearrangement A base-mediated 2,3-sigmatropic rearrangement of an activated tertiary allyl amine, to give a secondary homoallylic amine. http://purl.obolibrary.org/obo/RXNO_0000264 aza-Baylis-Hillman reaction http://purl.obolibrary.org/obo/RXNO_0000076 Baylis-Hillman reaction A carbon-carbon coupling of an imine to an activated alkene in the presence of a nucleophilic base to give an allylic amine. http://purl.obolibrary.org/obo/RXNO_0000265 aza-Wittig reaction http://purl.obolibrary.org/obo/RXNO_0000367 carbonyl compound to imine conversion Reaction of a carbonyl compound with a phosphazene to give an imine. http://purl.obolibrary.org/obo/RXNO_0000266 Fenton reaction http://purl.obolibrary.org/obo/RXNO_0000012 functional group oxidation An oxidation reaction involving Fenton's reagent. http://purl.obolibrary.org/obo/RXNO_0000268 Hantzsch pyridine synthesis http://purl.obolibrary.org/obo/RXNO_0000520 pyridine synthesis A ring-forming reaction between two equivalents of a beta-ketoester, an aldehyde and ammonia (or an ammonium salt), to give a dihydropyridine. The dihydropyridine can be oxidised to a pyridine using an oxidising agent. http://purl.obolibrary.org/obo/RXNO_0000269 alkyne-azide click reaction http://purl.obolibrary.org/obo/RXNO_0000018 1,3-dipolar cycloaddition A [3+2] cycloaddition reaction between an azide and an alkyne to give a 1,2,3-triazole, needing only heat to proceed. http://purl.obolibrary.org/obo/RXNO_0000270 copper(I)-catalyzed azide-alkyne cycloaddition http://purl.obolibrary.org/obo/MOP_0000715 [3+2] cycloaddition A [3+2] cycloaddition reaction between an azide and an alkyne to give a 1,2,3-triazole as a single regioisomer. http://purl.obolibrary.org/obo/RXNO_0000271 Fischer-Tropsch process http://purl.obolibrary.org/obo/RXNO_0000000 molecular skeleton joining reaction A process in which carbon monoxide and hydrogen ('syngas') are converted into various liquid hydrocarbons. http://purl.obolibrary.org/obo/RXNO_0000272 hydroformylation http://purl.obolibrary.org/obo/RXNO_0000000 molecular skeleton joining reaction The reaction of hydrogen and carbon monoxide with an alkene, to give an aldehyde, catalysed by a rhodium or cobalt catalyst. The process is equivalent to the formal addition of the H-C bond of formaldehyde across the double bond of an alkene. http://purl.obolibrary.org/obo/RXNO_0000273 retro-Diels-Alder reaction http://purl.obolibrary.org/obo/RXNO_0000205 ring breaking The reverse of a [4+2] cycloaddition reaction, in which an unsaturated six-membered ring compound fragments to give a diene and a compound containing a double or triple bond (a dienophile). http://purl.obolibrary.org/obo/RXNO_0000274 retro-aldol addition http://purl.obolibrary.org/obo/RXNO_0000073 cleaving reaction The reverse of an aldol addition, in which a beta-hydroxy ketone fragments to form a carbonyl compound and the enolate of an alpha-acidic carbonyl compound. http://purl.obolibrary.org/obo/RXNO_0000275 Stork-Crabtree hydrogenation http://purl.obolibrary.org/obo/RXNO_0000041 addition reaction step A hydrogenation in which a metal-ligating group distant from the reacting alkene directs the attack of hydrogen, giving preferentially one stereoisomer of the product. http://purl.obolibrary.org/obo/RXNO_0000276 Aufbau reaction http://purl.obolibrary.org/obo/RXNO_0000246 polymerisation reaction The insertion of alkenes (usually ethene) into the Al-C bond of an aluminium alkyl, to give a long-chain aluminium alkyl that can go on to react again, or can decompose into the corresponding terminal alkene. The addition of transition metals results in reliable production of high molecular weight polymers. http://purl.obolibrary.org/obo/RXNO_0000277 hydroalumination http://purl.obolibrary.org/obo/RXNO_0000294 hydrometallation The reaction of an aluminium alkyl with an alkene, to give an intermediate aluminium species that can give various products after work-up. http://purl.obolibrary.org/obo/RXNO_0000278 hydrovinylation http://purl.obolibrary.org/obo/RXNO_0000002 carbon-carbon coupling reaction The reaction of two alkenes to give an elongated alkene, employing a transition-metal-based catalyst. http://purl.obolibrary.org/obo/RXNO_0000279 1,4-hydrovinylation http://purl.obolibrary.org/obo/RXNO_0000278 hydrovinylation The reaction of a 1,3-diene with an alkene to give a 1,4-diene, usually employing a cobalt-based catalyst (see Hilt and Luers, Synthesis, 2002, 609). http://purl.obolibrary.org/obo/RXNO_0000280 alkene metathesis http://purl.obolibrary.org/obo/RXNO_0000204 multiple-bond metathesis A joining reaction in which two carbon-carbon double bonds are redistributed among two fragments, i.e. two alkenes. It is typically catalysed by a metal carbenoid, and proceeds via two four-membered intermediates (metallacyclobutanes). The reaction is driven by release of a low-MW alkene. http://purl.obolibrary.org/obo/RXNO_0000281 alkyne metathesis http://purl.obolibrary.org/obo/RXNO_0000204 multiple-bond metathesis A joining reaction in which two carbon-carbon triple bonds are redistributed among two fragments, i.e. two alkynes. It is catalysed by a metal carbenoid, and proceeds via two four-membered intermediates (metallacyclobutenes). The reaction is driven by release of a low-MW alkyne. http://purl.obolibrary.org/obo/RXNO_0000282 enyne metathesis http://purl.obolibrary.org/obo/RXNO_0000204 multiple-bond metathesis A joining reaction in which a carbon-carbon double bond and a carbon-carbon triple bond are redistributed among two fragments, i.e. an alkene and an alkyne. It is typically catalysed by a metal carbenoid, and proceeds via two four-membered intermediates (metallacyclobutenes). As a low-MW alkene is not released, the reaction is usually driven by formation of a ring. http://purl.obolibrary.org/obo/RXNO_0000283 ring-closing enyne metathesis http://purl.obolibrary.org/obo/RXNO_0000005 ring formation reaction step A joining reaction in which a carbon-carbon double bond and a carbon-carbon triple bond in the same molecule are redistributed to give a alkene-substituted cycloalkene. It is typically catalysed by a metal carbenoid, and proceeds via two four-membered intermediates (metallacyclobutanes). The reaction is driven by formation of the ring. http://purl.obolibrary.org/obo/RXNO_0000284 ring-opening metathesis http://purl.obolibrary.org/obo/RXNO_0000205 ring breaking A ring-breaking reaction in which two carbon-carbon double bonds are redistributed among two fragments, i.e. an alkene and a cycloalkene. It is typically catalysed by a metal carbenoid, and proceeds via two four-membered intermediates (metallacyclobutanes). The reaction is driven by release of ring strain in the cycloalkene. http://purl.obolibrary.org/obo/RXNO_0000285 Luche reaction http://purl.obolibrary.org/obo/RXNO_0000002 carbon-carbon coupling reaction A carbon-carbon coupling reaction where an aldehyde or ketone reacts with an allyl halide and zinc to give a homoallylic alcohol. http://purl.obolibrary.org/obo/RXNO_0000286 Luche reduction http://purl.obolibrary.org/obo/RXNO_0000037 functional group reduction The chemoselective reduction of an enone to give an allylic alcohol, using sodium borohydride and an lanthanoid chloride, typically cerium chloride. http://purl.obolibrary.org/obo/RXNO_0000287 Lindgren oxidation http://purl.obolibrary.org/obo/RXNO_0000012 functional group oxidation The oxidation of an aldehyde to a carboxylic acid with chlorite. http://purl.obolibrary.org/obo/RXNO_0000288 Rosenmund-von Braun reaction http://purl.obolibrary.org/obo/RXNO_0000002 carbon-carbon coupling reaction A carbon-carbon coupling reaction where an aryl halide reacts with copper(I) cyanide to give an aryl nitrile. http://purl.obolibrary.org/obo/RXNO_0000289 Woehler reaction http://purl.obolibrary.org/obo/RXNO_0000011 functional group modification The formation of urea from ammonium cyanate. Ammonium cyanate is unstable, and so is formed in situ from either (a) cyanic acid and ammonia, (b) a metal cyanate and an ammonium salt, or (c) a metal cyanate and ammonia. http://purl.obolibrary.org/obo/RXNO_0000290 hydrosilylation http://purl.obolibrary.org/obo/RXNO_0000041 addition reaction step The addition of a hydrosilane across the double bond of an alkene or alkyne to give a more substituted silane. Addition to an aldehyde or ketone produces a silyl ether. http://purl.obolibrary.org/obo/RXNO_0000291 hydroamination http://purl.obolibrary.org/obo/RXNO_0000041 addition reaction step The addition of the N-H bond of an amine across a double bond of an alkene or alkyne, to give a more substituted amine. http://purl.obolibrary.org/obo/RXNO_0000292 hydroboration http://purl.obolibrary.org/obo/RXNO_0000041 addition reaction step The addition of a boron hydride across a double bond of an alkene or alkyne. The boron usually adds to the less substituted carbon. http://purl.obolibrary.org/obo/RXNO_0000293 hydroboration-oxidation http://purl.obolibrary.org/obo/RXNO_0000041 addition reaction step The formal addition of water across a double bond of an alkene or alkyne by formation of an organoborane and in situ oxidation, typically with basic peroxide. The product is usually the less substituted alcohol. http://purl.obolibrary.org/obo/RXNO_0000294 hydrometallation http://purl.obolibrary.org/obo/RXNO_0000041 addition reaction step The reaction of any of a number of metal hydride species with an alkene or alkyne, to give an intermediate organometal species that can give various products after work-up. http://purl.obolibrary.org/obo/RXNO_0000295 hydrozirconation http://purl.obolibrary.org/obo/RXNO_0000294 hydrometallation The reaction of a organozirconium hydride with an alkene or alkyne, to give an intermediate zirconium species that can give various products after work-up. The zirconium reagent used is typically Schwartz's reagent, Cp2ZrHCl. http://purl.obolibrary.org/obo/RXNO_0000296 hydrostannylation http://purl.obolibrary.org/obo/RXNO_0000294 hydrometallation The reaction of a organotin hydride with an alkene or alkyne, to give an intermediate tin species that can give various products after work-up. http://purl.obolibrary.org/obo/RXNO_0000297 hydrotelluration http://purl.obolibrary.org/obo/RXNO_0000294 hydrometallation The reaction of a organotellurium hydride with an alkyne, to give a (usually (Z)-configured) vinyltellurium species. http://purl.obolibrary.org/obo/RXNO_0000298 Fetizon oxidation http://purl.obolibrary.org/obo/RXNO_0000012 functional group oxidation The oxidation of a primary alcohol to an aldehyde or a secondary alcohol to a ketone using Fetizon's reagent. http://purl.obolibrary.org/obo/RXNO_0000299 Vorbrueggen condensation http://purl.obolibrary.org/obo/RXNO_0000000 molecular skeleton joining reaction The substitution of an acylated sugar with a silylated base to give a nucleoside. http://purl.obolibrary.org/obo/RXNO_0000300 thiol-ene reaction http://purl.obolibrary.org/obo/RXNO_0000000 molecular skeleton joining reaction The addition of a thiol across the double bond of an alkene to give a thioether. http://purl.obolibrary.org/obo/RXNO_0000301 Yamamoto polymerisation http://purl.obolibrary.org/obo/RXNO_0000246 polymerisation reaction The nickel-catalysed carbon-carbon coupling of a dihaloaromatic compound or aromatic bistriflate to give a polymer. http://purl.obolibrary.org/obo/RXNO_0000302 thermal hydrosilylation http://purl.obolibrary.org/obo/RXNO_0000290 hydrosilylation The thermally induced addition of a hydrosilane across the double bond of an alkene or alkyne to give a more substituted silane, usually applied to cases where the hydrosilane is part of a silicon surface. http://purl.obolibrary.org/obo/RXNO_0000303 photohydrosilylation http://purl.obolibrary.org/obo/RXNO_0000290 hydrosilylation The photochemically induced addition of a hydrosilane across the double bond of an alkene or alkyne to give a more substituted silane, usually applied to cases where the hydrosilane is part of a silicon surface. The reaction uses UV irradiation and is usually initiated by an added photoactive compound such as a platinum catalyst. http://purl.obolibrary.org/obo/RXNO_0000304 Julia-Kocienski olefination http://purl.obolibrary.org/obo/RXNO_0000479 olefination A carbon-carbon coupling reaction between a tetrazole sulfone and an aldehyde or ketone to give a (typically trans) alkene. http://purl.obolibrary.org/obo/RXNO_0000305 seleno-Pummerer rearrangement http://purl.obolibrary.org/obo/RXNO_0000220 Pummerer rearrangement The conversion of a selenoxide with an alpha-hydrogen to an alpha-subtituted selenoether. http://purl.obolibrary.org/obo/RXNO_0000306 intramolecular Heck reaction http://purl.obolibrary.org/obo/RXNO_0000005 ring formation reaction step A carbon-carbon coupling reaction where an organohalide or triflate couples to an alkene in the same molecule, catalysed by palladium. http://purl.obolibrary.org/obo/RXNO_0000307 Mori-Ban indole synthesis http://purl.obolibrary.org/obo/RXNO_0000395 indole synthesis An intramolecular Heck reaction of an ortho-halo-aniline with an alkene, catalysed by palladium. http://purl.obolibrary.org/obo/RXNO_0000308 Yamaguchi lactonisation http://purl.obolibrary.org/obo/RXNO_0000346 oxacycle synthesis The intramolecular esterification of a carboxylic acid group with an alcohol group using 2,4,6-trichlorobenzoyl chloride (Yamaguchi reagent) - an intramolecular Yamaguchi esterification. http://purl.obolibrary.org/obo/RXNO_0000309 Yamaguchi esterification http://purl.obolibrary.org/obo/RXNO_0000331 substitution step The esterification of a carboxylic acid with an alcohol using 2,4,6-trichlorobenzoyl chloride (Yamaguchi reagent). http://purl.obolibrary.org/obo/RXNO_0000310 oxa-Diels-Alder reaction http://purl.obolibrary.org/obo/RXNO_0000313 hetero-Diels-Alder reaction A Diels-Alder reaction between a diene and an aldehyde or ketone to give a six-membered oxygen-containing ring compound. http://purl.obolibrary.org/obo/RXNO_0000311 Tsuji-Trost reaction http://purl.obolibrary.org/obo/MOP_0000422 allylation A carbon-carbon coupling reaction in which a nucleophile reacts with an allyl acetate, allyl halide, allyl carbonate, allyl carbamate, allyl phosphate, allyl sulfone or allyl nitro compound to give an allyl compound. The reaction is catalsed by Pd(0). http://purl.obolibrary.org/obo/RXNO_0000312 Clauson-Kaas reaction http://purl.obolibrary.org/obo/RXNO_0000497 pyrrole synthesis A ring rearrangement reaction where an amine reacts with a 2,5-dialkoxytetrahydrofuran to give a pyrrole. http://purl.obolibrary.org/obo/RXNO_0000313 hetero-Diels-Alder reaction http://purl.obolibrary.org/obo/RXNO_0000006 Diels-Alder reaction A [4+2] cycloaddition reaction where a diene (or heterocyclic analogue) reacts with a dienophile to form an unsaturated heterocyclic six-membered ring compound. http://purl.obolibrary.org/obo/RXNO_0000316 palladium-catalysed carbon-carbon coupling reaction http://purl.obolibrary.org/obo/RXNO_0000002 carbon-carbon coupling reaction A carbon-carbon coupling reaction that is catalysed by a palladium atom. http://purl.obolibrary.org/obo/RXNO_0000317 ester condensation reaction http://purl.obolibrary.org/obo/MOP_0000627 condensation reaction A condensation reaction that results in the production of an ester. http://purl.obolibrary.org/obo/RXNO_0000320 amino group deprotection http://purl.obolibrary.org/obo/RXNO_0000203 deprotection reaction A deprotection reaction where the reactive centre is an amino nitrogen atom. http://purl.obolibrary.org/obo/RXNO_0000321 amino group protection http://purl.obolibrary.org/obo/RXNO_0000078 protection reaction A protection reaction where the reactive centre is an amino nitrogen atom. http://purl.obolibrary.org/obo/RXNO_0000322 benzylamine protection http://purl.obolibrary.org/obo/RXNO_0000321 amino group protection An amino group protection where the amino nitrogen atom is protected by reaction with benzylamine. http://purl.obolibrary.org/obo/RXNO_0000323 hydroxyl group protection http://purl.obolibrary.org/obo/RXNO_0000078 protection reaction A protection reaction where the reactive centre is a hydroxyl oxygen atom. http://purl.obolibrary.org/obo/RXNO_0000324 benzyl ether protection http://purl.obolibrary.org/obo/RXNO_0000323 hydroxyl group protection A hydroxyl group protection where the hydroxyl oxygen atom is protected by formation of a benzyl ether. http://purl.obolibrary.org/obo/RXNO_0000325 carboxylic acid protection http://purl.obolibrary.org/obo/RXNO_0000078 protection reaction A protection reaction where the reactive centre is a carboxy oxygen. http://purl.obolibrary.org/obo/RXNO_0000326 Boc deprotection http://purl.obolibrary.org/obo/RXNO_0000320 amino group deprotection An amino group deprotection reaction where a tertbutoxycarbonyl group is removed in acid conditions. http://purl.obolibrary.org/obo/RXNO_0000327 benzylamine deprotection http://purl.obolibrary.org/obo/MOP_0000589 hydrogenation An amino group deprotection reaction where a benzylamine group is removed by hydrogenation. http://purl.obolibrary.org/obo/RXNO_0000328 silyl protection http://purl.obolibrary.org/obo/MOP_0003339 O-silylation A hydroxyl group protection where the hydroxyl oxygen atom is protected by formation of a silyl ether. http://purl.obolibrary.org/obo/RXNO_0000329 planned synthesis http://purl.obolibrary.org/obo/OBI_0000011 planned process An experimental procedure with the aim of producing a portion of a given compound or mixture. http://purl.obolibrary.org/obo/RXNO_0000330 acetate protection http://purl.obolibrary.org/obo/RXNO_0000323 hydroxyl group protection A hydroxyl group protection where the hydroxyl oxygen atom is protected by formation of an acetate ester. http://purl.obolibrary.org/obo/RXNO_0000331 substitution step http://purl.obolibrary.org/obo/RXNO_0000010 functional modification A functional modification step in which one singly-bonded substituent, but not a hydrogen, is replaced by another singly-bonded substituent. http://purl.obolibrary.org/obo/RXNO_0000332 aromatic substitution step http://purl.obolibrary.org/obo/RXNO_0000331 substitution step A substitution step where one singly-bonded substituent on an aromatic skeleton is replaced by another singly-bonded substituent. http://purl.obolibrary.org/obo/RXNO_0000333 Sandmeyer halogenation http://purl.obolibrary.org/obo/RXNO_0000021 Sandmeyer reaction An aromatic substitution reaction where an aryl diazonium salt reacts with a copper(I) halide to form an aromatic halide. http://purl.obolibrary.org/obo/RXNO_0000334 Sandmeyer pseudohalogenation http://purl.obolibrary.org/obo/RXNO_0000021 Sandmeyer reaction An aromatic substitution reaction where an aryl diazonium salt reacts with a copper(II) pseudohalide to form an aromatic pseudohalide. http://purl.obolibrary.org/obo/RXNO_0000335 reductive amination http://purl.obolibrary.org/obo/MOP_0000650 amination A functional group modification where a carbonyl oxygen is replaced by an amine. http://purl.obolibrary.org/obo/RXNO_0000337 nitro reduction to amine http://purl.obolibrary.org/obo/MOP_0000569 reduction A reduction reaction where a nitro group is reduced to an amino group. http://purl.obolibrary.org/obo/RXNO_0000338 amide reduction to amine http://purl.obolibrary.org/obo/MOP_0000569 reduction A reduction process where an amide is transformed into an amine. http://purl.obolibrary.org/obo/RXNO_0000339 alkene reduction to alkane http://purl.obolibrary.org/obo/MOP_0000589 hydrogenation A hydrogenation reaction where an alkene is reduced to an alkane. http://purl.obolibrary.org/obo/RXNO_0000340 amide N-alkylation http://purl.obolibrary.org/obo/MOP_0002369 N-alkylation An N-alkylation where the reactive centre is an amide nitrogen. http://purl.obolibrary.org/obo/RXNO_0000341 aniline N-alkylation http://purl.obolibrary.org/obo/MOP_0002369 N-alkylation An N-alkylation where the reactive centre is an aniline nitrogen. http://purl.obolibrary.org/obo/RXNO_0000342 nitrile reduction to amine http://purl.obolibrary.org/obo/MOP_0000569 reduction A reduction where a nitrile is replaced by an amine function. http://purl.obolibrary.org/obo/RXNO_0000343 imine reduction to amine http://purl.obolibrary.org/obo/MOP_0000569 reduction A reduction reaction where an imine function is replaced by an amine. http://purl.obolibrary.org/obo/RXNO_0000344 alkene oxidative cleavage http://purl.obolibrary.org/obo/MOP_0000581 alkene oxidation An alkene oxidation where the carbon-carbon double bond is cleaved. http://purl.obolibrary.org/obo/RXNO_0000345 heteroaryl N-alkylation http://purl.obolibrary.org/obo/MOP_0002369 N-alkylation An N-alkylation reaction where the reactive centre is an azacycle ring nitrogen. http://purl.obolibrary.org/obo/RXNO_0000346 oxacycle synthesis http://purl.obolibrary.org/obo/RXNO_0000349 heterocycle synthesis A ring formation reaction where the intended product contains an oxacycle that was not in any of the reactants. http://purl.obolibrary.org/obo/RXNO_0000347 azacycle synthesis http://purl.obolibrary.org/obo/RXNO_0000349 heterocycle synthesis A ring formation reaction where the intended product contains an azacycle that was not in any of the reactants. http://purl.obolibrary.org/obo/RXNO_0000348 thiacycle synthesis http://purl.obolibrary.org/obo/RXNO_0000349 heterocycle synthesis A ring formation reaction where the intended product contains an thiacycle that was not in any of the reactants. http://purl.obolibrary.org/obo/RXNO_0000349 heterocycle synthesis http://purl.obolibrary.org/obo/RXNO_0000005 ring formation reaction step A ring formation reaction where the intended product contains a heterocycle that was not in any of the reactants. http://purl.obolibrary.org/obo/RXNO_0000350 alkyne reduction to alkane http://purl.obolibrary.org/obo/MOP_0000589 hydrogenation A hydrogenation reaction where an alkyne is reduced to an alkane. http://purl.obolibrary.org/obo/RXNO_0000351 aryl reduction to cycloalkyl http://purl.obolibrary.org/obo/MOP_0000589 hydrogenation A hydrogenation reaction where an aryl ring is reduced to a cycloalkyl ring. http://purl.obolibrary.org/obo/RXNO_0000352 heteroaryl reduction to saturated heterocycle http://purl.obolibrary.org/obo/MOP_0000589 hydrogenation A hydrogenation reaction where a heteroaryl is reduced to a saturated heterocycle. http://purl.obolibrary.org/obo/RXNO_0000353 alcohol oxidation to carboxylic acid http://purl.obolibrary.org/obo/MOP_0000572 alcohol oxidation An alcohol oxidation where the alcohol centre is replaced with a carboxy group. http://purl.obolibrary.org/obo/RXNO_0000354 benzylic oxidation http://purl.obolibrary.org/obo/MOP_0000568 oxidation An oxidation reaction where a carbon centre bonded to the benzene ring is oxidized to a carboxyl group. http://purl.obolibrary.org/obo/RXNO_0000355 allylic oxidation http://purl.obolibrary.org/obo/MOP_0000568 oxidation An oxidation reaction where an allylic C-H bond is replaced by a C=O bond. http://purl.obolibrary.org/obo/RXNO_0000356 Jones oxidation http://purl.obolibrary.org/obo/MOP_0000572 alcohol oxidation An oxidation reaction where an alcohol is oxidized to the corresponding carbonyl compound by a dichromate ion. http://purl.obolibrary.org/obo/RXNO_0000357 N-acylation to amide http://purl.obolibrary.org/obo/MOP_0002479 N-acylation An acylation reaction where a nitrogen atom is acylated to form an amide. http://purl.obolibrary.org/obo/RXNO_0000358 N-acylation to urea http://purl.obolibrary.org/obo/MOP_0002479 N-acylation An acylation reaction where a nitrogen atom is acylated to form a urea. http://purl.obolibrary.org/obo/RXNO_0000359 N-acylation to carbamate http://purl.obolibrary.org/obo/MOP_0002479 N-acylation An N-acylation reaction where a nitrogen centre is acylated to form a carbamate. http://purl.obolibrary.org/obo/RXNO_0000360 O-acylation to ester http://purl.obolibrary.org/obo/MOP_0003479 O-acylation An O-acylation reaction where an oxygen centre is acylated to result in an ester. http://purl.obolibrary.org/obo/RXNO_0000361 Pinner reaction http://purl.obolibrary.org/obo/RXNO_0000011 functional group modification A functional group modification where a nitrile reacts with an alcohol under acid catalysis to form an amidine or ester. http://purl.obolibrary.org/obo/RXNO_0000362 nitrile alcoholysis http://purl.obolibrary.org/obo/MOP_0000568 oxidation An oxidation reaction where a nitrile reacts with an alcohol to form an alkyl imidate. http://purl.obolibrary.org/obo/RXNO_0000363 amide to imidoyl chloride conversion http://purl.obolibrary.org/obo/RXNO_0000011 functional group modification A functional group modification where an amide is converted to an imidoyl chloride. http://purl.obolibrary.org/obo/RXNO_0000364 alcohol to halide conversion http://purl.obolibrary.org/obo/RXNO_0000011 functional group modification A functional group modification where an alcohol is converted to a halide. http://purl.obolibrary.org/obo/RXNO_0000365 carboxylic acid to acid chloride conversion http://purl.obolibrary.org/obo/RXNO_0000011 functional group modification A functional group modification where a carboxylic acid is converted to an acid chloride. http://purl.obolibrary.org/obo/RXNO_0000366 nitrile to acid conversion http://purl.obolibrary.org/obo/RXNO_0000011 functional group modification A functional group modification where a nitrile is transformed into a carboxylic acid. http://purl.obolibrary.org/obo/RXNO_0000367 carbonyl compound to imine conversion http://purl.obolibrary.org/obo/RXNO_0000011 functional group modification A functional group modification where a carbonyl compound is converted to an imine. http://purl.obolibrary.org/obo/RXNO_0000368 Crabbé homologation http://purl.obolibrary.org/obo/MOP_0000581 alkene oxidation Oxidation of an alkene to an allene by heating with formaldehyde, an amine and an inorganic salt. http://purl.obolibrary.org/obo/RXNO_0000369 Friedel-Crafts reaction http://purl.obolibrary.org/obo/RXNO_0000002 carbon-carbon coupling reaction A carbon-carbon coupling reaction between an arene and a carbonyl compound (an acylation) or an alkyl compound that can form a carbocation (an alkylation) to form a substituted arene. http://purl.obolibrary.org/obo/RXNO_0000370 Demko-Sharpless reaction http://purl.obolibrary.org/obo/RXNO_0000011 functional group modification A functional group modification of a nitrile to a 1H-tetrazole by addition of sodium azide. http://purl.obolibrary.org/obo/RXNO_0000371 Griess reaction http://purl.obolibrary.org/obo/RXNO_0000013 diazotisation A diazotisation that proceeds by the addition of nitrous acid, nitric acid and water, resulting in a diazonium nitrate salt. http://purl.obolibrary.org/obo/RXNO_0000372 heteroaryl N-arylation http://purl.obolibrary.org/obo/MOP_0002411 N-arylation An N-arylation reaction where the reactive centre is an azacycle ring nitrogen. http://purl.obolibrary.org/obo/RXNO_0000373 functional group addition step http://purl.obolibrary.org/obo/MOP_0000566 formation of covalent bond with group A planned reaction step in which a covalent bond is formed between the molecular skeleton and a functional group and where the skeletal bond order is unchanged. http://purl.obolibrary.org/obo/RXNO_0000374 Chan-Lam coupling http://purl.obolibrary.org/obo/MOP_0000411 arylation Arylation of an amine or an alcohol with an arylboronic acid, stannane or siloxane in air with a copper acetate catalyst. http://purl.obolibrary.org/obo/RXNO_0000376 Eschweiler-Clarke methylation http://purl.obolibrary.org/obo/MOP_0002364 N-methylation N-methylation of a primary or secondary amine with formic acid and formaldehyde to yield a tertiary amine. http://purl.obolibrary.org/obo/RXNO_0000377 Scholl reaction http://purl.obolibrary.org/obo/RXNO_0000002 carbon-carbon coupling reaction Coupling of two aromatic rings in the presence of a Lewis acid catalyst. http://purl.obolibrary.org/obo/RXNO_0000378 intramolecular Scholl reaction http://purl.obolibrary.org/obo/RXNO_0000377 Scholl reaction Scholl reaction within a single molecule to form a larger ring system. http://purl.obolibrary.org/obo/RXNO_0000379 intermolecular Scholl reaction http://purl.obolibrary.org/obo/RXNO_0000377 Scholl reaction Scholl reaction between two aromatic molecules to form a single molecule. http://purl.obolibrary.org/obo/RXNO_0000380 Robinson annulation http://purl.obolibrary.org/obo/RXNO_0000052 fused-ring-system formation Reaction of a cyclohexanone with methyl vinyl ketone to form a fused-ring cyclohexenone. It is a Michael reaction followed by an intramolecular aldol condensation. http://purl.obolibrary.org/obo/RXNO_0000381 Tiffeneau-Demjanov rearrangement http://purl.obolibrary.org/obo/RXNO_0000025 rearrangement step Rearrangement of a beta-amino alcohol to yield a carbonyl compound. In the first step the amine is diazotised by reaction with nitrous acid. http://purl.obolibrary.org/obo/RXNO_0000382 Demjanov rearrangement http://purl.obolibrary.org/obo/RXNO_0000331 substitution step Substitution reaction of a primary amine via deazotisation to yield a mixture of the corresponding primary alcohol and secondary alcohol. http://purl.obolibrary.org/obo/RXNO_0000384 cyclic alpha-haloketone Favorskii rearrangement http://purl.obolibrary.org/obo/RXNO_0000385 Favorskii rearrangement Base-catalysed rearrangement of a cyclic alpha-haloketone to the ring-contracted cyclic carboxylic acid. http://purl.obolibrary.org/obo/RXNO_0000385 Favorskii rearrangement http://purl.obolibrary.org/obo/RXNO_0000025 rearrangement step Base-catalysed rearrangement of an alpha-haloketone to a carboxylic acid or ester or amide. http://purl.obolibrary.org/obo/RXNO_0000386 Wallach degradation http://purl.obolibrary.org/obo/RXNO_0000206 ring contraction Favorskii rearrangement of a cyclic alpha-dibromoketone followed by decarboxylation to yield a ring-contracted cyclic ketone. http://purl.obolibrary.org/obo/RXNO_0000387 Seyferth-Gilbert homologation http://purl.obolibrary.org/obo/MOP_0000714 carbonyl oxidation to alkyne Reaction of a carbonyl compound with a dimethyl diazomethyl phosphonate under basic conditions to yield an alkyne. http://purl.obolibrary.org/obo/RXNO_0000388 Seyferth-Gilbert aldehyde homologation http://purl.obolibrary.org/obo/RXNO_0000387 Seyferth-Gilbert homologation Reaction of an aldehyde with a dimethyl diazomethyl phosphonate under basic conditions to yield a terminal alkyne. http://purl.obolibrary.org/obo/RXNO_0000389 Seyferth-Gilbert ketone homologation http://purl.obolibrary.org/obo/RXNO_0000387 Seyferth-Gilbert homologation Reaction of a ketone with a dimethyl diazomethyl phosphonate under basic conditions to yield a terminal alkyne. http://purl.obolibrary.org/obo/RXNO_0000390 Seyferth-Gilbert-Bestmann homologation http://purl.obolibrary.org/obo/RXNO_0000388 Seyferth-Gilbert aldehyde homologation Seyferth-Gilbert aldehyde homologation where the Seyferth-Gilbert reagent is generated in situ by reaction with methanol and potassium carbonate. http://purl.obolibrary.org/obo/RXNO_0000391 Knorr pyrazole synthesis http://purl.obolibrary.org/obo/MOP_0000628 molecular dehydration reaction Synthesis of a pyrazole by condensation of a 1,3-dicarbonyl compound with a hydrazine, hydrazide, semicarbazide or aminoguanidine. http://purl.obolibrary.org/obo/RXNO_0000392 pyrazole synthesis http://purl.obolibrary.org/obo/RXNO_0000347 azacycle synthesis A reaction in which the intended product is a pyrazole that was not present in any of the reactants. http://purl.obolibrary.org/obo/RXNO_0000393 quinoline synthesis http://purl.obolibrary.org/obo/RXNO_0000347 azacycle synthesis A reaction in which the intended product is a quinoline that was not present in any of the reactants. http://purl.obolibrary.org/obo/RXNO_0000394 Knorr quinoline synthesis http://purl.obolibrary.org/obo/RXNO_0000393 quinoline synthesis Synthesis of an alpha-hydroxyquinoline by reaction of a beta-ketoester and an arylamine then dehydration with concentrated sulfuric acid. http://purl.obolibrary.org/obo/RXNO_0000395 indole synthesis http://purl.obolibrary.org/obo/RXNO_0000347 azacycle synthesis A reaction in which the intended product is an indole that was not present in any of the reactants. http://purl.obolibrary.org/obo/RXNO_0000396 Larock indole synthesis http://purl.obolibrary.org/obo/RXNO_0000395 indole synthesis Palladium-catalysed synthesis of a 2,3-substituted indole by reaction of an ortho-iodoaniline with an internal alkyne. http://purl.obolibrary.org/obo/RXNO_0000397 Pechmann pyrazole synthesis http://purl.obolibrary.org/obo/RXNO_0000392 pyrazole synthesis Reaction of an organic diazo compound with an acetylene to yield a pyrazole. http://purl.obolibrary.org/obo/RXNO_0000398 benzimidazole synthesis http://purl.obolibrary.org/obo/RXNO_0000052 fused-ring-system formation A reaction in which the intended product is a benzimidazole that was not present in any of the reactants. http://purl.obolibrary.org/obo/RXNO_0000399 Phillips benzimidazole synthesis http://purl.obolibrary.org/obo/RXNO_0000398 benzimidazole synthesis Reaction of an ortho-diaminobenzene with a carboxylic acid under heat to yield a benzimidazole. http://purl.obolibrary.org/obo/RXNO_0000400 pyrimidine synthesis http://purl.obolibrary.org/obo/RXNO_0000347 azacycle synthesis A reaction in which the intended product is a pyrimidine that was not present in any of the reactants. http://purl.obolibrary.org/obo/RXNO_0000401 triazine synthesis http://purl.obolibrary.org/obo/RXNO_0000347 azacycle synthesis A reaction in which the intended product is a triazine that was not present in any of the reactants. http://purl.obolibrary.org/obo/RXNO_0000402 Pinner pyrimidine synthesis http://purl.obolibrary.org/obo/RXNO_0000400 pyrimidine synthesis Reaction of a 1,3-dicarbonyl compound with an amidine to yield a pyrimidine. http://purl.obolibrary.org/obo/RXNO_0000403 Pinner triazine synthesis http://purl.obolibrary.org/obo/RXNO_0000401 triazine synthesis Reaction of aryl amidines or halogenated aliphatics amidines with phosgene to yield a 2-hydroxy-4,6-diaryl-s-triazine with loss of ammonia. http://purl.obolibrary.org/obo/RXNO_0000404 oxa-Pictet-Spengler reaction http://purl.obolibrary.org/obo/MOP_0000627 condensation reaction Cyclisation-condensation of a beta-arylethanol with an aldehyde to yield an ortho,peri-fused aryl-oxacycle. http://purl.obolibrary.org/obo/RXNO_0000405 Prilezhaev epoxidation http://purl.obolibrary.org/obo/MOP_0000671 epoxidation Epoxidation of an alkene by reaction with a peroxy acid. http://purl.obolibrary.org/obo/RXNO_0000406 Appel halogenation http://purl.obolibrary.org/obo/RXNO_0000364 alcohol to halide conversion Conversion of an alcohol to an alkyl halide with triphenylphosphine and a halide source. http://purl.obolibrary.org/obo/RXNO_0000407 Appel iodination http://purl.obolibrary.org/obo/RXNO_0000406 Appel halogenation Conversion of an alcohol to an alkyl iodide with triphenylphosphine and tetraiodomethane. http://purl.obolibrary.org/obo/RXNO_0000408 Appel chlorination http://purl.obolibrary.org/obo/RXNO_0000406 Appel halogenation Conversion of an alcohol to an alkyl chloride with triphenylphosphine and tetrachloromethane. http://purl.obolibrary.org/obo/RXNO_0000409 Appel bromination http://purl.obolibrary.org/obo/RXNO_0000406 Appel halogenation Conversion of an alcohol to an alkyl bromide with triphenylphosphine and tetrabromomethane or bromine. http://purl.obolibrary.org/obo/RXNO_0000410 Hofmann rearrangement http://purl.obolibrary.org/obo/RXNO_0000105 end-of-chain chain shortening Rearrangement of a primary carboxylic amide to an isocyanate. http://purl.obolibrary.org/obo/RXNO_0000411 Hofmann reaction http://purl.obolibrary.org/obo/RXNO_0000105 end-of-chain chain shortening Conversion of a primary carboxylic amide to the lower homologue primary amine. The first step is the Hofmann rearrangement http://purl.obolibrary.org/obo/RXNO_0000412 Newman-Kwart rearrangement http://purl.obolibrary.org/obo/RXNO_0000011 functional group modification Rearrangement of an O-aryl thiocarbamate to an S-aryl thiocarbamate by migration of the aryl group. http://purl.obolibrary.org/obo/RXNO_0000413 Zincke nitration http://purl.obolibrary.org/obo/MOP_0000556 nitration Substitution of phenol ortho- or para-bromo or iodo groups by a nitro group on treatment with nitrous acid or a nitrite in acetic acid. http://purl.obolibrary.org/obo/RXNO_0000414 haloethanoate ester-aldehyde Darzens reaction http://purl.obolibrary.org/obo/RXNO_0000077 Darzens reaction A coupling of an aldehyde with an alpha-haloethanoate ester to form the next homologous aldehyde. http://purl.obolibrary.org/obo/RXNO_0000415 haloethanoate ester-ketone Darzens reaction http://purl.obolibrary.org/obo/RXNO_0000077 Darzens reaction A coupling of a ketone with an alpha-haloethanoate ester to replace the oxo group with a formyl group. http://purl.obolibrary.org/obo/RXNO_0000418 phthalimide protection http://purl.obolibrary.org/obo/RXNO_0000321 amino group protection Protection of a primary amino group by reaction with phthalic anhydride. http://purl.obolibrary.org/obo/RXNO_0000419 phthalimide deprotection http://purl.obolibrary.org/obo/RXNO_0000320 amino group deprotection Conversion of a phthalimide into the corresponding primary amine. http://purl.obolibrary.org/obo/RXNO_0000420 Kröhnke pyridine synthesis http://purl.obolibrary.org/obo/RXNO_0000520 pyridine synthesis Condensation of a 1,5-diketone with ammonium acetate in acetic acid to form a pyridine. http://purl.obolibrary.org/obo/RXNO_0000421 Gattermann chlorination http://purl.obolibrary.org/obo/RXNO_0000022 Gattermann halogenation A Gattermann halogenation where the aryl diazonium salt reacts with copper powder and hydrochloric acid to yield an aromatic chloride. http://purl.obolibrary.org/obo/RXNO_0000422 Gattermann bromination http://purl.obolibrary.org/obo/RXNO_0000022 Gattermann halogenation A Gattermann halogenation where the aryl diazonium salt reacts with copper powder and hydrobromic acid to yield an aromatic bromide. http://purl.obolibrary.org/obo/RXNO_0000426 aldehyde Barbier reaction http://purl.obolibrary.org/obo/RXNO_0000084 Barbier reaction A joining reaction between an aldehyde and an alkyl halide or aryl halide or vinyl halide or allyl halide in the presence of metal to give a secondary alcohol. http://purl.obolibrary.org/obo/RXNO_0000427 ketone Barbier reaction http://purl.obolibrary.org/obo/RXNO_0000084 Barbier reaction A joining reaction between an ketone and an alkyl halide or aryl halide or vinyl halide or allyl halide in the presence of metal to give a tertiary alcohol. http://purl.obolibrary.org/obo/RXNO_0000428 pivaloyl protection http://purl.obolibrary.org/obo/RXNO_0000323 hydroxyl group protection Protection of a hydroxy group by reaction with pivaloyl chloride, resulting in formation of a pivaloyl ester. http://purl.obolibrary.org/obo/RXNO_0000429 pivaloyl deprotection http://purl.obolibrary.org/obo/RXNO_0000430 hydroxy group deprotection A hydroxy group deprotection where a pivalate group is removed in acid or base conditions. http://purl.obolibrary.org/obo/RXNO_0000430 hydroxy group deprotection http://purl.obolibrary.org/obo/RXNO_0000203 deprotection reaction A deprotection reaction where the reactive centre is an oxygen atom. http://purl.obolibrary.org/obo/RXNO_0000431 carboxylic acid to primary alcohol reduction http://purl.obolibrary.org/obo/MOP_0000569 reduction A carboxylic acid reduction where the product is the corresponding primary alcohol. http://purl.obolibrary.org/obo/RXNO_0000432 tert-butyl protection http://purl.obolibrary.org/obo/RXNO_0000325 carboxylic acid protection A carboxy group protection where the product is a tert-butyl ester. http://purl.obolibrary.org/obo/RXNO_0000433 carboxy group deprotection http://purl.obolibrary.org/obo/RXNO_0000203 deprotection reaction A deprotection reaction where the reactive centre is a carboxy oxygen atom. http://purl.obolibrary.org/obo/RXNO_0000434 tert-butyl ester deprotection http://purl.obolibrary.org/obo/RXNO_0000433 carboxy group deprotection A deprotection reaction where the reactant is a tert-butyl ester and the product is a carboxylic acid. http://purl.obolibrary.org/obo/RXNO_0000435 methyl ester deprotection http://purl.obolibrary.org/obo/RXNO_0000433 carboxy group deprotection A deprotection reaction where the reactant is a methyl ester and the product is a carboxylic acid. http://purl.obolibrary.org/obo/RXNO_0000436 ethyl ester deprotection http://purl.obolibrary.org/obo/RXNO_0000433 carboxy group deprotection A deprotection reaction where the reactant is an ethyl ester and the product is a carboxylic acid. http://purl.obolibrary.org/obo/RXNO_0000437 molecular transformation objective http://purl.obolibrary.org/obo/IAO_0000005 objective specification An objective specification that describes how a molecule's skeleton and substituents are to be transformed by a given experiment. http://purl.obolibrary.org/obo/RXNO_0000438 molecular skeleton cleaving objective http://purl.obolibrary.org/obo/RXNO_0000437 molecular transformation objective A molecular transformation specification that specifies that atoms should be lost from the molecular skeleton. http://purl.obolibrary.org/obo/RXNO_0000439 molecular ring formation objective http://purl.obolibrary.org/obo/RXNO_0000437 molecular transformation objective A molecular transformation specification that specifies that the product should contain a ring that was not in any of the reactants. http://purl.obolibrary.org/obo/RXNO_0000440 molecular skeleton joining objective http://purl.obolibrary.org/obo/RXNO_0000437 molecular transformation objective A molecular transformation specification that specifies that atoms should be added to the molecular skeleton. http://purl.obolibrary.org/obo/RXNO_0000441 molecular rearrangement objective http://purl.obolibrary.org/obo/RXNO_0000437 molecular transformation objective A molecular transformation specification that specifies that the number of rings and number of skeletal atoms should be preserved and that one or more atoms or groups of atoms move from one atom to another. http://purl.obolibrary.org/obo/RXNO_0000442 functional modification objective http://purl.obolibrary.org/obo/RXNO_0000437 molecular transformation objective A molecular transformation specification that specifies that the substituents of a molecule should be changed but the number of atoms in the skeleton and their connectivity, but not necessarily the bond orders, should remain the same. http://purl.obolibrary.org/obo/RXNO_0000443 Sakurai reaction http://purl.obolibrary.org/obo/MOP_0000422 allylation Reaction of allyltrimethylsilane with a carbon electrophile to allylate the carbon electrophile. http://purl.obolibrary.org/obo/RXNO_0000444 Fries rearrangement http://purl.obolibrary.org/obo/RXNO_0000025 rearrangement step Rearrangement of the acyl group in a phenolate ester to the ortho- and/or para-position. It is catalysed by a Lewis acid. http://purl.obolibrary.org/obo/RXNO_0000445 ortho-Fries rearrangement http://purl.obolibrary.org/obo/RXNO_0000444 Fries rearrangement Rearrangement of the acyl group in a phenolate ester to the ortho-position. http://purl.obolibrary.org/obo/RXNO_0000446 para-Fries rearrangement http://purl.obolibrary.org/obo/RXNO_0000444 Fries rearrangement Rearrangement of the acyl group in a phenolate ester to the para-position. http://purl.obolibrary.org/obo/RXNO_0000447 Duff reaction http://purl.obolibrary.org/obo/MOP_0000003 formylation Formylation of a phenol or aromatic amine with hexamethylenetetramine in acidic conditions. http://purl.obolibrary.org/obo/RXNO_0000448 molecular chain lengthening objective http://purl.obolibrary.org/obo/RXNO_0000440 molecular skeleton joining objective A molecular skeleton joining adjective that is satisfied by a chain part of a molecular skeleton being lengthened. http://purl.obolibrary.org/obo/RXNO_0000449 molecular ring breaking objective http://purl.obolibrary.org/obo/RXNO_0000437 molecular transformation objective A molecular skeleton transformation objective that is satisfied by a reaction where the product has fewer rings than the reactants. http://purl.obolibrary.org/obo/RXNO_0000450 molecular ring contraction objective http://purl.obolibrary.org/obo/RXNO_0000437 molecular transformation objective A molecular skeleton transformation objective that is satisfied by a reaction where an existing ring is reduced in size. http://purl.obolibrary.org/obo/RXNO_0000451 aldehyde Sakurai reaction http://purl.obolibrary.org/obo/RXNO_0000212 Sakurai reaction, aldehyde or ketone A carbon-carbon coupling reaction in which an aldehyde reacts with allyltrimethylsilane to form a homoallylic alcohol. http://purl.obolibrary.org/obo/RXNO_0000452 ketone Sakurai reaction http://purl.obolibrary.org/obo/RXNO_0000212 Sakurai reaction, aldehyde or ketone A carbon-carbon coupling reaction in which a ketone reacts with allyltrimethylsilane to form a homoallylic alcohol. http://purl.obolibrary.org/obo/RXNO_0000453 functional group modification objective http://purl.obolibrary.org/obo/RXNO_0000442 functional modification objective A molecular skeleton transformation objective that is satisfied by a reaction in which a functional group undergoes a change that does not affect the number of atoms in (or connectivity of) the skeleton of the molecule. http://purl.obolibrary.org/obo/RXNO_0000454 end-of-chain chain shortening objective http://purl.obolibrary.org/obo/RXNO_0000438 molecular skeleton cleaving objective A molecular skeleton transformation objective that is satisfied by a reaction in which a single skeletal atom is removed from the end of a chain. http://purl.obolibrary.org/obo/RXNO_0000455 functional reduction objective http://purl.obolibrary.org/obo/RXNO_0000453 functional group modification objective A functional group modification objective that is satisfied by a reaction in which a functional group is reduced. http://purl.obolibrary.org/obo/RXNO_0000456 addition objective http://purl.obolibrary.org/obo/RXNO_0000442 functional modification objective A functional modification objective that is satisfied by a reaction in which two or more groups of atoms are added to the molecule, resulting in a change of skeletal bond order. http://purl.obolibrary.org/obo/RXNO_0000457 molecular ring expansion objective http://purl.obolibrary.org/obo/RXNO_0000437 molecular transformation objective A molecular transformation objective that is satisfied by a reaction in which an existing skeletal ring is increased in size. http://purl.obolibrary.org/obo/RXNO_0000458 molecular ring rearrangement objective http://purl.obolibrary.org/obo/RXNO_0000437 molecular transformation objective A molecular transformation objective that is satisfied by a reaction in which the number of skeletal rings in a molecule stays the same but the connectivity of the atoms in at least one ring changes. http://purl.obolibrary.org/obo/RXNO_0000459 acetoacetic ester synthesis http://purl.obolibrary.org/obo/RXNO_0000000 molecular skeleton joining reaction A carbon-carbon coupling reaction between a beta-ketoester and an alkyl halide to yield an alpha-alkylated ester. http://purl.obolibrary.org/obo/RXNO_0000461 intermolecular acyloin condensation http://purl.obolibrary.org/obo/RXNO_0000085 acyloin condensation A reductive coupling reaction between two ester groups in different molecules to give an acyloin (an alpha-hydroxyketone). http://purl.obolibrary.org/obo/RXNO_0000462 molecular extrusion objective http://purl.obolibrary.org/obo/RXNO_0000438 molecular skeleton cleaving objective A molecular transformation objective that is satisfied by a cleaving reaction in which a skeletal atom or group of atoms is removed from the middle of a molecule. http://purl.obolibrary.org/obo/RXNO_0000463 molecular fragmentation objective http://purl.obolibrary.org/obo/RXNO_0000438 molecular skeleton cleaving objective A molecular transformation objective that is satisfied by a reaction in which the parent molecule breaks up into three or more products. http://purl.obolibrary.org/obo/RXNO_0000464 Pauson-Khand reaction http://purl.obolibrary.org/obo/MOP_0000720 [2+2+1] cycloaddition A [2+2+1] cycloaddition between an alkyne, an alkene and carbon monoxide to form an alpha-beta-unsaturated cyclopentenone. http://purl.obolibrary.org/obo/RXNO_0000465 fused-ring-system formation objective http://purl.obolibrary.org/obo/RXNO_0000439 molecular ring formation objective A molecular transformation objective that is satisfied by a reaction in which a fused ring system is present in a product that was not present in any of the reactants. http://purl.obolibrary.org/obo/RXNO_0000466 polymerisation objective http://purl.obolibrary.org/obo/RXNO_0000440 molecular skeleton joining objective A molecular transformation objective that is satisfied by a reaction in which a large number of monomers react together to product a polymer consisting of repeating units. http://purl.obolibrary.org/obo/RXNO_0000467 Algar-Flynn-Oyamada reaction http://purl.obolibrary.org/obo/RXNO_0000346 oxacycle synthesis A fused-ring-system formation reaction where a flavonol is produced by oxidation of a chalcone with alkaline hydrogen peroxide. http://purl.obolibrary.org/obo/RXNO_0000468 molecular substitution objective http://purl.obolibrary.org/obo/RXNO_0000442 functional modification objective A molecular transformation objective that is satisfied by a reaction in which one singly-bonded substituent, but not a hydrogen, is replaced by another singly-bonded substituent. http://purl.obolibrary.org/obo/RXNO_0000470 Allan-Robinson flavone synthesis http://purl.obolibrary.org/obo/RXNO_0000475 Allan-Robinson reaction Reaction of ortho-hydroxyaryl ketones with aromatic carboxylic acid anhydrides to yield a flavone. http://purl.obolibrary.org/obo/RXNO_0000471 Allan-Robinson isoflavone synthesis http://purl.obolibrary.org/obo/RXNO_0000475 Allan-Robinson reaction Reaction of ortho-hydroxyaryl ketones with aromatic carboxylic acid anhydrides to yield an isoflavone. http://purl.obolibrary.org/obo/RXNO_0000472 Amadori rearrangement http://purl.obolibrary.org/obo/RXNO_0000025 rearrangement step Rearrangement of an aldose N-glycoside to a ketose N-glycoside by acid or base catalysis. http://purl.obolibrary.org/obo/RXNO_0000473 Arens-van Dorp synthesis http://purl.obolibrary.org/obo/RXNO_0000000 molecular skeleton joining reaction Reaction of a ketone with ethoxyacetylene to form an alkoxyethynyl alcohol. http://purl.obolibrary.org/obo/RXNO_0000474 Auwers synthesis http://purl.obolibrary.org/obo/RXNO_0000346 oxacycle synthesis Ring expansion of a 2-bromo-2-(alpha-bromobenzyl)-1-benzofuran to a flavonol in alcoholic alkali. http://purl.obolibrary.org/obo/RXNO_0000475 Allan-Robinson reaction http://purl.obolibrary.org/obo/RXNO_0000346 oxacycle synthesis Reaction of ortho-hydroxyaryl ketones with aromatic acid anhydrides to yield a flavone or isoflavone. http://purl.obolibrary.org/obo/RXNO_0000476 Meyer-Schuster rearrangement http://purl.obolibrary.org/obo/RXNO_0000025 rearrangement step Rearrangement of a propargyl alcohol to an alpha,beta-unsaturated carbonyl compound via an allene intermediate to yield the gamma-substituted product. http://purl.obolibrary.org/obo/RXNO_0000477 Rupe rearrangement http://purl.obolibrary.org/obo/RXNO_0000025 rearrangement step Rearrangement of a propargyl alcohol to an alpha,beta-unsaturated carbonyl compound via an enyne intermediate to yield the beta-substituted product. http://purl.obolibrary.org/obo/RXNO_0000478 Still-Gennari modification http://purl.obolibrary.org/obo/RXNO_0000056 Horner-Wadsworth-Emmons reaction A Horner-Wadsworth-Emmons reaction that uses phosphonates with electron-withdrawing groups and dissociating conditions to produce predominantly Z-olefins. http://purl.obolibrary.org/obo/RXNO_0000479 olefination http://purl.obolibrary.org/obo/RXNO_0000000 molecular skeleton joining reaction A molecular skeleton joining reaction where the connection formed is a carbon-carbon double bond. http://purl.obolibrary.org/obo/RXNO_0000480 Tebbe olefination http://purl.obolibrary.org/obo/RXNO_0000479 olefination Reaction of an aldehyde or ketone or carboxylic ester or amide with the Tebbe reagent to yield an olefin or an enol ether or an enamine. http://purl.obolibrary.org/obo/RXNO_0000481 Myers-Saito cyclisation http://purl.obolibrary.org/obo/RXNO_0000005 ring formation reaction step Cyclization of a enynyl allene to yield a toluene biradical with radical centres on the methyl group and at the meta position. http://purl.obolibrary.org/obo/RXNO_0000482 Schmittel cyclisation http://purl.obolibrary.org/obo/RXNO_0000005 ring formation reaction step Cyclization of a enynyl allene to yield a 1-methyl-5-methylenecyclopenta-1,3-diene biradical with radical centres on the methyl group and methylene group. http://purl.obolibrary.org/obo/RXNO_0000483 Baudisch reaction http://purl.obolibrary.org/obo/RXNO_0000373 functional group addition step Copper-catalysed reaction of benzene with a nitrosylating agent and hydrogen peroxide to form an o-nitrosophenol. http://purl.obolibrary.org/obo/RXNO_0000484 deprotection objective http://purl.obolibrary.org/obo/RXNO_0000442 functional modification objective A functional modification objective that is satisfied by deprotecting some functional group. http://purl.obolibrary.org/obo/RXNO_0000485 protection objective http://purl.obolibrary.org/obo/RXNO_0000442 functional modification objective A functional modification objective that is satisfied by protecting some functional group. http://purl.obolibrary.org/obo/RXNO_0000486 molecular skeleton elimination objective http://purl.obolibrary.org/obo/RXNO_0000442 functional modification objective A functional modification objective that is satisfied by a reaction in which two or more groups of atoms are removed from the molecule, resulting in a change of skeletal bond order. http://purl.obolibrary.org/obo/RXNO_0000487 molecular skeleton insertion objective http://purl.obolibrary.org/obo/RXNO_0000440 molecular skeleton joining objective A molecular skeleton joining objective that is satisfied by a reaction in which one or more atoms are added to the middle of a chain. http://purl.obolibrary.org/obo/RXNO_0000488 joining with rearrangement objective http://purl.obolibrary.org/obo/RXNO_0000440 molecular skeleton joining objective A molecular skeleton joining objective that is satisfied by a reaction in which one or more atoms are added to the molecular skeleton and a skeletal rearrangement occurs. http://purl.obolibrary.org/obo/RXNO_0000489 functional group addition objective http://purl.obolibrary.org/obo/RXNO_0000442 functional modification objective A functional modification objective that is satisfied by a reaction in which a covalent bond is formed between the molecular skeleton and a functional group and where the skeletal bond order is unchanged. http://purl.obolibrary.org/obo/RXNO_0000490 functional oxidation objective http://purl.obolibrary.org/obo/RXNO_0000453 functional group modification objective A functional group modification objective that is satisfied by a reaction in which a functional group is oxidised. http://purl.obolibrary.org/obo/RXNO_0000491 interrupted Nazarov cyclisation http://purl.obolibrary.org/obo/RXNO_0000005 ring formation reaction step Cyclisation of a propargyl alpha,beta-unsaturated ketone where the reactant rearranges to an allenyl vinyl ketone, followed by a Nazarov cyclisation in which a nucleophile 'intercepts' the intermediate carbocation to yield a cyclopentenone substituted at the alpha position opposite the double bond. http://purl.obolibrary.org/obo/RXNO_0000492 Bamberger rearrangement http://purl.obolibrary.org/obo/RXNO_0000025 rearrangement step Rearrangement of an N-phenylhydroxamine in acid to yield a para-aminophenol. http://purl.obolibrary.org/obo/RXNO_0000493 Bart reaction http://purl.obolibrary.org/obo/RXNO_0000332 aromatic substitution step Reaction of an aromatic diazonium compound with an alkali arsenite in the presence of copper or silver to yield an aromatic arsonic acid. http://purl.obolibrary.org/obo/RXNO_0000494 Bartoli indole synthesis http://purl.obolibrary.org/obo/RXNO_0000395 indole synthesis Reaction of an ortho-substituted nitroarene with a vinyl Grignard reagent to yield a 7-substituted indole. http://purl.obolibrary.org/obo/RXNO_0000495 Barton olefination http://purl.obolibrary.org/obo/RXNO_0000479 olefination Reaction of an aldehyde or ketone with a thioaldehyde or thioketone via a 1,3,4-thiadiazoline intermediate to yield an olefin. http://purl.obolibrary.org/obo/RXNO_0000496 Barton-Zard reaction http://purl.obolibrary.org/obo/RXNO_0000497 pyrrole synthesis Reaction of a nitroalkene with an alpha-isocyanoacetate to yield a substituted pyrrole. http://purl.obolibrary.org/obo/RXNO_0000497 pyrrole synthesis http://purl.obolibrary.org/obo/RXNO_0000347 azacycle synthesis A reaction in which the intended product is a pyrrole that was not present in any of the reactants. http://purl.obolibrary.org/obo/RXNO_0000498 Béchamp reduction http://purl.obolibrary.org/obo/RXNO_0000037 functional group reduction Reduction of an aromatic nitro compound to the corresponding arene by iron in some form in aqueous acid. http://purl.obolibrary.org/obo/RXNO_0000499 Beirut reaction http://purl.obolibrary.org/obo/RXNO_0000108 ring expansion Reaction of a benzofurazan 1-oxide with an enamine or enolate to yield a quinoxaline-1,4-dioxide. http://purl.obolibrary.org/obo/RXNO_0000500 Bénary reaction http://purl.obolibrary.org/obo/RXNO_0000000 molecular skeleton joining reaction Reaction of a beta-aminovinylketone with a Grignard reagent to yield a substituted alpha,beta-unsaturated carbonyl compound. http://purl.obolibrary.org/obo/RXNO_0000501 Feist-Bénary synthesis http://purl.obolibrary.org/obo/RXNO_0000346 oxacycle synthesis Reaction of an alpha-haloketone or alpha-haloether with a 1,3-dicarbonyl compound in the presence of pyridine to yield a substituted furan. http://purl.obolibrary.org/obo/RXNO_0000502 Boulton-Katritzky rearrangement http://purl.obolibrary.org/obo/RXNO_0000202 ring rearrangement Rearrangement of a mancude eight-membered system containing a pentacycle into a different pentacycle where two of the ring atoms are ring atoms in the original molecule. http://purl.obolibrary.org/obo/RXNO_0000503 monocyclic Boulton-Katritzky rearrangement http://purl.obolibrary.org/obo/RXNO_0000502 Boulton-Katritzky rearrangement Rearrangement of an azapentacycle containing a -N= system where there is an unsaturated three-heavy-atom substituent XYZ on the substituent double-bonded to the nitrogen, to a new azapentacycle where the pivotal nitrogen has broken its single bond and formed a new bond with atom Z. http://purl.obolibrary.org/obo/RXNO_0000504 bicyclic Boulton-Katritzky rearrangement http://purl.obolibrary.org/obo/RXNO_0000502 Boulton-Katritzky rearrangement Rearrangement of a mancude bicyclo[4.3.0] compound with an unsaturated two-heavy-atom substituent on the six-membered ring alpha to the bridgehead to form a new mancude bicyclo[4.3.0] compound where the five-membered ring has been formed from the two-heavy-atom substituent and the original five-membered ring has been broken. http://purl.obolibrary.org/obo/RXNO_0000505 Mukaiyama-Hoshino method http://purl.obolibrary.org/obo/RXNO_0000011 functional group modification Reaction of a primary nitro compound with phenyl isocynatate and triethylamine to yield a nitrile oxide. http://purl.obolibrary.org/obo/RXNO_0000506 Nef synthesis http://purl.obolibrary.org/obo/RXNO_0000000 molecular skeleton joining reaction Reaction of an aldehyde or ketone with a sodium acetylide to yield a propargyl alcohol. http://purl.obolibrary.org/obo/RXNO_0000507 Krapcho decarboxylation http://purl.obolibrary.org/obo/RXNO_0000105 end-of-chain chain shortening Reaction of an ester with an electron-withdrawing group alpha- to the ester functionality with a metal halide or pseudohalide to yield the shorter homologous system. http://purl.obolibrary.org/obo/RXNO_0000508 Cadogan cyclization http://purl.obolibrary.org/obo/RXNO_0000052 fused-ring-system formation Reaction of an aromatic nitro compound with an unsaturated substituent at the alpha-position to form a fused-ring nitrogen heterocycle. http://purl.obolibrary.org/obo/RXNO_0000509 Cadogan indole synthesis http://purl.obolibrary.org/obo/RXNO_0000508 Cadogan cyclization A Cadogan cyclization that results in an indole. http://purl.obolibrary.org/obo/RXNO_0000510 Benkeser reduction http://purl.obolibrary.org/obo/MOP_0000589 hydrogenation Addition of hydrogen atoms to unsaturated rings by means of alkali metals in low-molecular weight amines. http://purl.obolibrary.org/obo/RXNO_0000511 Madelung indole synthesis http://purl.obolibrary.org/obo/MOP_0000628 molecular dehydration reaction Reaction of an N-(2-alkylphenyl)alkanamide with strong base to form an indole. http://purl.obolibrary.org/obo/RXNO_0000512 Smith indole synthesis http://purl.obolibrary.org/obo/RXNO_0000395 indole synthesis Reaction of a N-(2-alkylphenyl)-trimethylsilylamine with two equivalents of organolithium and an ester or carboxylic acid to form an indole. http://purl.obolibrary.org/obo/RXNO_0000513 Mumm rearrangement http://purl.obolibrary.org/obo/RXNO_0000025 rearrangement step Rearrangement of an acyl imidate to form a carboximide. http://purl.obolibrary.org/obo/RXNO_0000515 Bergmann azlactone peptide synthesis http://purl.obolibrary.org/obo/RXNO_0000000 molecular skeleton joining reaction Reaction of an acetylated amino acid with an aldehyde then with a second amino acid, then hydrogenation and hydrolysis to form a dipeptide. It proceeds via an azlactone intermediate. http://purl.obolibrary.org/obo/RXNO_0000516 Bergmann degradation http://purl.obolibrary.org/obo/RXNO_0000517 terminal amino-acid residue cleaving reaction Removal of a terminal amino acid residue from a peptide by benzoylation, azidation, treatment with benzyl alcohol, hydrogenation and hydrolysis. http://purl.obolibrary.org/obo/RXNO_0000517 terminal amino-acid residue cleaving reaction http://purl.obolibrary.org/obo/RXNO_0000073 cleaving reaction Removal of a terminal amino acid residue from a peptide. http://purl.obolibrary.org/obo/RXNO_0000518 acridine synthesis http://purl.obolibrary.org/obo/RXNO_0000347 azacycle synthesis Ring formation reaction where the intended product is an acridine. http://purl.obolibrary.org/obo/RXNO_0000519 Bernthsen acridine synthesis http://purl.obolibrary.org/obo/RXNO_0000518 acridine synthesis Reaction of a diarylamine in an organic acid or anhydride in the presence of zinc chloride to yield a 9-substituted acridine. http://purl.obolibrary.org/obo/RXNO_0000520 pyridine synthesis http://purl.obolibrary.org/obo/RXNO_0000347 azacycle synthesis Ring formation reaction where the intended product is a pyridine. http://purl.obolibrary.org/obo/RXNO_0000521 carbazole synthesis http://purl.obolibrary.org/obo/RXNO_0000347 azacycle synthesis Ring formation reaction where the intended product is a carbazole. http://purl.obolibrary.org/obo/RXNO_0000522 Betti reaction http://purl.obolibrary.org/obo/RXNO_0000000 molecular skeleton joining reaction Reaction of a phenol, an aromatic aldehyde and a primary aromatic or heterocyclic amine to yield a Betti's base, also known as an alpha-aminobenzylphenol. http://purl.obolibrary.org/obo/RXNO_0000523 Bischler-Möhlau indole synthesis http://purl.obolibrary.org/obo/RXNO_0000395 indole synthesis Reaction of a terminal hydroxyketone or terminal halogenoketone with an aromatic amine to yield a 2-substituted indole. http://purl.obolibrary.org/obo/RXNO_0000524 Camps quinoline synthesis http://purl.obolibrary.org/obo/RXNO_0000393 quinoline synthesis Cyclisation of an o-acylaminoacetophenone in alcoholic sodium hydroxide to form a substituted hydroxyquinoline. http://purl.obolibrary.org/obo/RXNO_0000525 Castro-Stephens coupling http://purl.obolibrary.org/obo/RXNO_0000316 palladium-catalysed carbon-carbon coupling reaction Palladium-catalysed coupling of copper(I) acetylides with aryl halides to yield arylacetylenes. http://purl.obolibrary.org/obo/RXNO_0000526 Chichibabin pyridine synthesis http://purl.obolibrary.org/obo/RXNO_0000520 pyridine synthesis Reaction of carbonyl compounds with ammonia or an amine to yield a pyridine. http://purl.obolibrary.org/obo/RXNO_0000527 Chichibabin reaction http://purl.obolibrary.org/obo/MOP_0000650 amination Reaction of an azacycle with an alkali-metal amide to yield an aminated azacycle. http://purl.obolibrary.org/obo/RXNO_0000528 Bodroux reaction http://purl.obolibrary.org/obo/RXNO_0000011 functional group modification Reaction of a carboxylic ester with a magnesium iodide alkylamide to yield a carboxamide. http://purl.obolibrary.org/obo/RXNO_0000529 Bogert-Cook synthesis http://purl.obolibrary.org/obo/RXNO_0000052 fused-ring-system formation Condensation of beta-phenylethylmagnesium bromide with a cyclohexanone followed by cyclisation and dehydration in concentrated sulfuric acid to yield an octahydrophenanthrene. http://purl.obolibrary.org/obo/RXNO_0000530 Bohn-Schmidt reaction http://purl.obolibrary.org/obo/RXNO_0000373 functional group addition step Reaction of a hydroxylated anthraquinone with fuming sulfuric acid or sulfuric acid in boric acid in the presence of a mercury or selenium catalyst to form a more hydroxylated anthraquinone. http://purl.obolibrary.org/obo/RXNO_0000531 Boord olefin synthesis http://purl.obolibrary.org/obo/RXNO_0000479 olefination Etherification of an aldehyde followed by bromination and reaction with a Grignard reagent followed by treatment with zinc to eliminate the halogen and alkoxy groups to produce an olefin. http://purl.obolibrary.org/obo/RXNO_0000532 Borsche-Drechsel cyclisation http://purl.obolibrary.org/obo/RXNO_0000521 carbazole synthesis Rearrangement of a cyclohexanone phenylhydrazone followed by oxidation to yield a carbazole. http://purl.obolibrary.org/obo/RXNO_0000533 Bouveault aldehyde synthesis http://purl.obolibrary.org/obo/RXNO_0000070 chain lengthening Reaction of an organomagnesium or organolithium compound with an N,N'-disubstituted formamide to yield the next homologous aldehyde. http://purl.obolibrary.org/obo/RXNO_0000534 Bradsher cyclisation http://purl.obolibrary.org/obo/RXNO_0000052 fused-ring-system formation Diels-Alder reaction of a dienophile with a cationic aromatic azadiene to yield a bridged-ring system. http://purl.obolibrary.org/obo/RXNO_0000535 Bradsher reaction http://purl.obolibrary.org/obo/RXNO_0000052 fused-ring-system formation Reaction of an ortho-acyldiarylmethane, catalysed by acid, to yield an anthracene. http://purl.obolibrary.org/obo/RXNO_0000536 Parham cyclisation http://purl.obolibrary.org/obo/RXNO_0000052 fused-ring-system formation Reaction of a bromoarene that has an electrophilic group at the para-position with lithium bromide or lithium iodide followed by intramolecular cyclisation to yield a fused-ring system. http://purl.obolibrary.org/obo/RXNO_0000537 Quelet reaction http://purl.obolibrary.org/obo/RXNO_0000373 functional group addition step Reaction of an aliphatic aldehyde with a phenolic ether and hydrochloric acid to yield an alpha-chloroalkylphenolic ether. http://purl.obolibrary.org/obo/RXNO_0000538 Chugaev reaction http://purl.obolibrary.org/obo/RXNO_0000123 molecular skeleton elimination reaction Elimination of a water molecule from a secondary alcohol to yield an olefin. http://purl.obolibrary.org/obo/RXNO_0000539 Cope elimination http://purl.obolibrary.org/obo/RXNO_0000123 molecular skeleton elimination reaction Elimination of a hydroxylamine from an amine oxide by pyrolysis to yield an olefin. http://purl.obolibrary.org/obo/RXNO_0000540 Sugasawa reaction http://purl.obolibrary.org/obo/RXNO_0000373 functional group addition step Reaction of an aniline with a nitrile in the presence of boron trichloride and a Lewis acid to yield an ortho-acylated aniline. http://purl.obolibrary.org/obo/RXNO_0000541 palladium-catalysed Kumada coupling http://purl.obolibrary.org/obo/RXNO_0000316 palladium-catalysed carbon-carbon coupling reaction A cross-coupling reaction between a Grignard reagent and an activated (aryl or vinyl) halide or triflate. The reaction is catalysed by a palladium catalyst. http://purl.obolibrary.org/obo/RXNO_0000542 nickel-catalysed Kumada coupling http://purl.obolibrary.org/obo/RXNO_0000144 Kumada coupling A cross-coupling reaction between a Grignard reagent and an activated (aryl or vinyl) halide or triflate. The reaction is catalysed by a nickel catalyst. http://purl.obolibrary.org/obo/RXNO_0000543 Eastwood reaction http://purl.obolibrary.org/obo/RXNO_0000123 molecular skeleton elimination reaction Reaction of a 1,2-diol with triethoxymethane under heat to yield an olefin. http://purl.obolibrary.org/obo/RXNO_0000544 Saegusa oxidation http://purl.obolibrary.org/obo/RXNO_0000123 molecular skeleton elimination reaction Reaction of silyl enol ethers with palladium acetate in acetonitrile to yield an alpha,beta-unsaturated ketone. http://purl.obolibrary.org/obo/RXNO_0000545 Sandmeyer diphenylurea isatin synthesis http://purl.obolibrary.org/obo/RXNO_0000395 indole synthesis Reaction of diphenylthiourea with lead carbonate and potassium cyanide to form a cyanoformidine followed by ring closure and acid hydrolysis to yield isatin. http://purl.obolibrary.org/obo/RXNO_0000546 Sandmeyer isonitrosoacetanilide isatin synthesis http://purl.obolibrary.org/obo/RXNO_0000395 indole synthesis Reaction of aniline, hydroxylamine and chloral hydrate to form an aniline intermediate followed by cyclization in acid and hydrolysis to yield isatin. http://purl.obolibrary.org/obo/RXNO_0000547 Sarett oxidation http://purl.obolibrary.org/obo/MOP_0000572 alcohol oxidation Oxidation of an alcohol with a pyridine-chromium trioxide complex to yield a carbonyl compound. http://purl.obolibrary.org/obo/RXNO_0000548 Sarett primary alcohol oxidation http://purl.obolibrary.org/obo/MOP_0000573 primary alcohol oxidation to aldehyde Oxidation of a primary alcohol with a pyridine-chromium trioxide complex to yield an aldehyde. http://purl.obolibrary.org/obo/RXNO_0000549 Sarett secondary alcohol oxidation http://purl.obolibrary.org/obo/MOP_0000574 secondary alcohol oxidation to ketone Oxidation of a secondary alcohol with a pyridine-chromium trioxide complex to yield a ketone. http://purl.obolibrary.org/obo/RXNO_0000550 Collins oxidation http://purl.obolibrary.org/obo/MOP_0000572 alcohol oxidation Oxidation of a primary alcohol with a pyridine-chromium trioxide complex in dichloromethane to yield an aldehyde. http://purl.obolibrary.org/obo/RXNO_0000551 reductive imination http://purl.obolibrary.org/obo/MOP_0000555 imination A functional group modification where a carbonyl oxygen is replaced by an imine. http://purl.obolibrary.org/obo/RXNO_0000552 Leuckart aldehyde reaction http://purl.obolibrary.org/obo/RXNO_0000101 Leuckart reaction Reductive amination of an aldehyde with ammonium formate or formamide to form an amine. http://purl.obolibrary.org/obo/RXNO_0000553 Leuckart ketone reaction http://purl.obolibrary.org/obo/RXNO_0000101 Leuckart reaction Reductive amination of a ketone with ammonium formate or formamide to form an amine. http://purl.obolibrary.org/obo/RXNO_0000555 Appel bromination with bromine http://purl.obolibrary.org/obo/RXNO_0000409 Appel bromination Conversion of an alcohol to an alkyl bromide with triphenylphosphine and bromine. http://purl.obolibrary.org/obo/RXNO_0000556 Corey-Fuchs terminal dibromoolefination http://purl.obolibrary.org/obo/RXNO_0000479 olefination Reaction of an aldehyde with tetrabromomethane and triphenylphosphine to yield a terminal dibromoolefin. http://purl.obolibrary.org/obo/CHEBI_51277 thioester http://purl.obolibrary.org/obo/CHEBI_36587 carbonyl compound A compound of general formula RC(=O)SR'. Compare with thionoester, RC(=S)OR'. http://purl.obolibrary.org/obo/CHEBI_16385 organic sulfide http://purl.obolibrary.org/obo/CHEBI_23367 molecular entity Compounds having the structure RSR (R =/= H). Such compounds were once called thioethers. http://purl.obolibrary.org/obo/CHEBI_50887 haloarene http://purl.obolibrary.org/obo/CHEBI_24472 halohydrocarbon A compound derived from an arene by replacing a hydrogen atom with a halogen atom. http://purl.obolibrary.org/obo/CHEBI_172874 phenylsilane http://purl.obolibrary.org/obo/CHEBI_25713 organosilicon compound An organosilicon compound that is benzene in which a hydrogen is replaced by a silyl group. http://purl.obolibrary.org/obo/RXNO_0000514 Chapman rearrangement http://purl.obolibrary.org/obo/RXNO_0000025 rearrangement step Rearrangement of an aryl imino ether to yield an N,N-diaryl amide. http://purl.obolibrary.org/obo/MOP_0001369 dealkylation http://purl.obolibrary.org/obo/MOP_0001458 deorganylation Breaking of a covalent bond between an alkyl group and a substrate. http://purl.obolibrary.org/obo/CHEBI_139588 alpha-hydroxy ketone http://purl.obolibrary.org/obo/CHEBI_52395 oxyketone An alpha-oxyketone that has a hydroxy group as the alpha-oxy moiety. http://purl.obolibrary.org/obo/RXNO_0000554 Appel bromination with tetrabromomethane http://purl.obolibrary.org/obo/RXNO_0000409 Appel bromination Conversion of an alcohol to an alkyl bromide with triphenylphosphine and tetrabromomethane. http://purl.obolibrary.org/obo/RXNO_0000095 Fischer-Hepp rearrangement http://purl.obolibrary.org/obo/RXNO_0000025 rearrangement step The rearrangement of an aromatic nitrosamine to a para-nitrosoaniline. http://purl.obolibrary.org/obo/RXNO_0000657 carbonyl group protection http://purl.obolibrary.org/obo/RXNO_0000078 protection reaction A protection reaction where the reactive centre is a carbonyl oxygen. http://purl.obolibrary.org/obo/RXNO_0000658 acetal protection http://purl.obolibrary.org/obo/RXNO_0000657 carbonyl group protection The acid-catalyzed formation of an acetal (or ketal) to protect a carbonyl group by nucleophilic addition of an alcohol to an aldehyde (or ketone) with the elimination of water. http://purl.obolibrary.org/obo/RXNO_0000661 Tsuji-Wilkinson decarbonylation http://purl.obolibrary.org/obo/RXNO_0000105 end-of-chain chain shortening The Tsuji-Wilkinson decarbonylation reaction is a method for the decarbonylation of aldehydes and some acyl chlorides. http://purl.obolibrary.org/obo/RXNO_0000662 Corey-Seebach reaction http://purl.obolibrary.org/obo/RXNO_0000011 functional group modification A chemical reaction in which ketones are synthesized from formaldehyde or other aldehydes, involving a temporary repolarization of a carbonyl group. http://purl.obolibrary.org/obo/RXNO_0000663 nitroxide exchange reaction http://purl.obolibrary.org/obo/RXNO_0000011 functional group modification Nitroxide exchange reactions are based on thermal C–O bond homolysis of alkoxyamines, which leads to transient carbon-centred radicals and persistent nitroxide radicals. Usually these carbon centred radicals are quickly trapped by the nitroxide radicals and reform the alkoxyamines. http://purl.obolibrary.org/obo/RXNO_0000664 Baeyer pyridine synthesis http://purl.obolibrary.org/obo/RXNO_0000011 functional group modification The conversion of pyran or pyrone (pyranone) derivatives to the corresponding pyridine derivative. http://purl.obolibrary.org/obo/RXNO_0000665 Corey-Kim oxidation http://purl.obolibrary.org/obo/RXNO_0000012 functional group oxidation Oxidation of primary and secondary alcohols via their alkoxysulfonium salts. Upon the addition of base, the salt rearranges intramolecularly to aldehydes and ketones, respectively. http://purl.obolibrary.org/obo/RXNO_0000666 Corey-Suggs oxidation http://purl.obolibrary.org/obo/RXNO_0000012 functional group oxidation Oxidation of primary and secondary alcohols to aldehydes and ketones, respectively, through the use of pyridinium chlorochromate (PCC). http://purl.obolibrary.org/obo/RXNO_0000667 Corey-Schmidt oxidation http://purl.obolibrary.org/obo/RXNO_0000012 functional group oxidation Oxidation of primary and secondary alcohols to aldehydes and ketones, respectively, through the use of pyridinium dichromate (PDC). http://purl.obolibrary.org/obo/RXNO_0000668 Albright-Goldman oxidation http://purl.obolibrary.org/obo/RXNO_0000012 functional group oxidation A particularly mild oxidation method in which, for example, dimethyl sulfoxide and acetic anhydride can be used as oxidizing agents to selectively produce aldehydes from primary alcohols without further oxidation to carboxylic acids. Analogously, secondary alcohols can be oxidized to form ketones. http://purl.obolibrary.org/obo/RXNO_0000669 Rubottom oxidation http://purl.obolibrary.org/obo/RXNO_0000012 functional group oxidation The Rubottom oxidation is a useful, high-yielding chemical reaction between silyl enol ethers and peroxy acids to give the corresponding α-hydroxy carbonyl product. http://purl.obolibrary.org/obo/RXNO_0000673 IBX oxidation http://purl.obolibrary.org/obo/RXNO_0000012 functional group oxidation Oxidation of alcohols to the corresponding carbonyl product using 2-iodoxybenzoic acid (IBX) as oxidizing agent. http://purl.obolibrary.org/obo/RXNO_0000643 Prato reaction http://purl.obolibrary.org/obo/RXNO_0000018 1,3-dipolar cycloaddition A 1,3-dipolar cycloaddition reaction where a fullerene reacts with an aldehyde and an amino acid to form a pyrrolidinofullerene. http://purl.obolibrary.org/obo/RXNO_0000644 Piancatelli rearrangement http://purl.obolibrary.org/obo/RXNO_0000025 rearrangement step A rearrangement of a 2-furylcarbinol to a 4-hydroxycyclopentenone. It is acid-catalysed. http://purl.obolibrary.org/obo/RXNO_0000645 retro-Prato reaction http://purl.obolibrary.org/obo/RXNO_0000205 ring breaking A ring-breaking reaction where a pyrrolidinofullerene yields a fullerene. The substituted fullerene is heated with a dipolarophile and a catalyst. http://purl.obolibrary.org/obo/RXNO_0000646 Bingel reaction http://purl.obolibrary.org/obo/RXNO_0000052 fused-ring-system formation A cycloaddition where a fullerene reacts with diethyl bromomalonate to form a methanofullerene. http://purl.obolibrary.org/obo/RXNO_0000647 Wacker cyclisation http://purl.obolibrary.org/obo/RXNO_0000018 1,3-dipolar cycloaddition A cyclisation where a hydroxyl group acts as the nucleophile in a Wacker-Tsuji oxidation accompanied by beta-hydride elimination, forming a ring. http://purl.obolibrary.org/obo/RXNO_0000648 aza-Wacker cyclisation http://purl.obolibrary.org/obo/RXNO_0000018 1,3-dipolar cycloaddition A cyclisation where an amino group acts as the nucleophile in a Wacker-Tsuji oxidation accompanied by beta-hydride elimination, forming a ring. http://purl.obolibrary.org/obo/RXNO_0000680 Fukuyama reduction http://purl.obolibrary.org/obo/RXNO_0000037 functional group reduction The reduction of a thioester to an aldehyde by a silyl hydride in the presence of catalytic amounts of palladium. http://purl.obolibrary.org/obo/MOP_0000003 formylation http://purl.obolibrary.org/obo/MOP_0000479 acylation Formation of a covalent bond between a substrate and a formyl group. http://purl.obolibrary.org/obo/MOP_0000339 silylation http://purl.obolibrary.org/obo/MOP_0000566 formation of covalent bond with group Formation of a covalent bond between a substrate and an silyl group. http://purl.obolibrary.org/obo/MOP_0000369 alkylation http://purl.obolibrary.org/obo/MOP_0000410 hydrocarbylation Formation of a covalent bond between a substrate and an alkyl group. http://purl.obolibrary.org/obo/MOP_0000410 hydrocarbylation http://purl.obolibrary.org/obo/MOP_0000458 organylation Formation of a covalent bond between a substrate and a hydrocarbyl group. http://purl.obolibrary.org/obo/MOP_0000411 arylation http://purl.obolibrary.org/obo/MOP_0000410 hydrocarbylation Formation of a covalent bond between a substrate and an aryl group. http://purl.obolibrary.org/obo/MOP_0000422 allylation http://purl.obolibrary.org/obo/MOP_0000410 hydrocarbylation Formation of a covalent bond between a substrate and an allyl group. http://purl.obolibrary.org/obo/MOP_0000458 organylation http://purl.obolibrary.org/obo/MOP_0000566 formation of covalent bond with group Formation of a covalent bond between a substrate and an organyl group. http://purl.obolibrary.org/obo/MOP_0000479 acylation http://purl.obolibrary.org/obo/MOP_0000458 organylation Formation of a covalent bond between a substrate and an acyl group. http://purl.obolibrary.org/obo/MOP_0000539 sulfonylation http://purl.obolibrary.org/obo/MOP_0000566 formation of covalent bond with group Formation of a covalent bond between a substrate and a sulfonyl group. http://purl.obolibrary.org/obo/MOP_0000543 molecular process http://purl.obolibrary.org/obo/BFO_0000015 process A process in which at least one of the participants is a molecule. http://purl.obolibrary.org/obo/MOP_0000550 halogenation http://purl.obolibrary.org/obo/MOP_0000566 formation of covalent bond with group Formation of a covalent bond between a substrate and a halo group. http://purl.obolibrary.org/obo/MOP_0000555 imination http://purl.obolibrary.org/obo/MOP_0000802 formation of covalent bond with nitrogen centre Formation of a covalent bond between a substrate and an imino group. http://purl.obolibrary.org/obo/MOP_0000556 nitration http://purl.obolibrary.org/obo/MOP_0000566 formation of covalent bond with group Formation of a covalent bond between a substrate and a nitro group. http://purl.obolibrary.org/obo/MOP_0000561 cyclization http://purl.obolibrary.org/obo/MOP_0000543 molecular process Formation of a ring in a molecule from a chain by formation of a new bond. http://purl.obolibrary.org/obo/MOP_0000562 cycloaddition http://purl.obolibrary.org/obo/MOP_0000561 cyclization A molecular process where two or more unsaturated molecules or parts of the same molecule combine to form a cyclic adduct in which there is a net reduction of bond multiplicity. http://purl.obolibrary.org/obo/MOP_0000563 [2+2] cycloaddition http://purl.obolibrary.org/obo/MOP_0000562 cycloaddition A cycloaddition in which each participant contributes two electrons to the transformation of reactants to products. http://purl.obolibrary.org/obo/MOP_0000564 cycloelimination http://purl.obolibrary.org/obo/MOP_0000543 molecular process A molecular process in which a cyclic system decomposes into two or more unsaturated molecules or parts of the same molecule and there is a net increase in bond multiplicity. http://purl.obolibrary.org/obo/MOP_0000565 [4+2] cycloaddition http://purl.obolibrary.org/obo/MOP_0000562 cycloaddition A cycloaddition in which one participant contributes four electrons and the other participant contributes two electrons to the transformation of reactants to products. http://purl.obolibrary.org/obo/MOP_0000566 formation of covalent bond with group http://purl.obolibrary.org/obo/MOP_0000543 molecular process Formation of a covalent bond between a substrate and a group. http://purl.obolibrary.org/obo/MOP_0000567 breaking of covalent bond with group http://purl.obolibrary.org/obo/MOP_0000543 molecular process Breaking of a covalent bond between a substrate and a group. http://purl.obolibrary.org/obo/MOP_0000568 oxidation http://purl.obolibrary.org/obo/MOP_0000543 molecular process The complete, net removal of one or mole electrons from a molecular entity, corresponding to an increase in the oxidation number of any atom within any substrate. http://purl.obolibrary.org/obo/MOP_0000569 reduction http://purl.obolibrary.org/obo/MOP_0000543 molecular process The complete transfer of one or more electrons to a molecular entity. http://purl.obolibrary.org/obo/MOP_0000570 electron attachment http://purl.obolibrary.org/obo/MOP_0000569 reduction The transfer of an electron to a molecular entity, resulting in a molecular entity of increased negative charge. http://purl.obolibrary.org/obo/MOP_0000571 aldehyde reduction http://purl.obolibrary.org/obo/MOP_0000569 reduction A reduction in which an aldehyde is reduced to form a primary alcohol. http://purl.obolibrary.org/obo/MOP_0000572 alcohol oxidation http://purl.obolibrary.org/obo/MOP_0000568 oxidation An oxidation process where an alcohol is transformed into a carbonyl compound. http://purl.obolibrary.org/obo/MOP_0000573 primary alcohol oxidation to aldehyde http://purl.obolibrary.org/obo/MOP_0000572 alcohol oxidation An oxidation process where a primary alcohol is transformed into an aldehyde. http://purl.obolibrary.org/obo/MOP_0000574 secondary alcohol oxidation to ketone http://purl.obolibrary.org/obo/MOP_0000572 alcohol oxidation An oxidation process where a secondary alcohol is transformed into a ketone. http://purl.obolibrary.org/obo/MOP_0000575 amine oxidation http://purl.obolibrary.org/obo/MOP_0000706 oxidation at nitrogen An oxidation process where an amine is transformed into an imine. http://purl.obolibrary.org/obo/MOP_0000576 imine reduction http://purl.obolibrary.org/obo/MOP_0000569 reduction A reduction process where an imine is transformed into an amine. http://purl.obolibrary.org/obo/MOP_0000577 ester reduction http://purl.obolibrary.org/obo/MOP_0000569 reduction A reduction process where the oxidation state carbonyl carbon in the ester functionality is reduced. http://purl.obolibrary.org/obo/MOP_0000578 ester reduction to aldehyde http://purl.obolibrary.org/obo/MOP_0000577 ester reduction An ester reduction where the product is the corresponding aldehyde. http://purl.obolibrary.org/obo/MOP_0000579 ester reduction to primary alcohol http://purl.obolibrary.org/obo/MOP_0000577 ester reduction An ester reduction where the product is the corresponding primary alcohol. http://purl.obolibrary.org/obo/MOP_0000580 ketone reduction http://purl.obolibrary.org/obo/MOP_0000569 reduction A reduction process where a ketone is reduced to a secondary alcohol. http://purl.obolibrary.org/obo/MOP_0000581 alkene oxidation http://purl.obolibrary.org/obo/MOP_0000568 oxidation An oxidation process where the oxidation state of at least one doubly-bonded carbon atom increases. http://purl.obolibrary.org/obo/MOP_0000582 alkene oxidation to 1,2-diol http://purl.obolibrary.org/obo/MOP_0000581 alkene oxidation An alkene oxidation where the product is the corresponding 1,2-diol. http://purl.obolibrary.org/obo/MOP_0000583 alkene ozonolysis http://purl.obolibrary.org/obo/RXNO_0000344 alkene oxidative cleavage An alkene oxidation where the reagent is ozone and the product is the corresponding ozonide. http://purl.obolibrary.org/obo/MOP_0000584 primary alkene oxidation to carboxylic acid and carbon dioxide http://purl.obolibrary.org/obo/RXNO_0000344 alkene oxidative cleavage An alkene oxidation process where the reactant is a primary alkene and the products are carboxylic acid and carbon dioxide. This can be achieved with a warm, acidic solution of potassium permanganate. http://purl.obolibrary.org/obo/MOP_0000585 tertiary alkene oxidation to carboxylic acid and ketone http://purl.obolibrary.org/obo/RXNO_0000344 alkene oxidative cleavage An alkene oxidation where the reactant is a tertiary alkene and the products are the corresponding carboxylic acid and ketone. This can be achieved with a warm, acidic solution of potassium permanganate. http://purl.obolibrary.org/obo/MOP_0000586 secondary, non-terminal alkene oxidation to aldehydes http://purl.obolibrary.org/obo/RXNO_0000344 alkene oxidative cleavage An alkene oxidation process where the reactant is a secondary alkene and the products are the corresponding aldehydes. This can be achieved with warm, acidic potassium permanganate. http://purl.obolibrary.org/obo/MOP_0000587 secondary terminal alkene oxidation to ketone and carbon dioxide http://purl.obolibrary.org/obo/RXNO_0000344 alkene oxidative cleavage An alkene oxidation process where the reactant is a secondary terminal alkene and the products are carbon dioxide and the corresponding ketone. This can be achieved by warm, acidic potassium permanganate solution. http://purl.obolibrary.org/obo/MOP_0000588 quaternary alkene oxidation to ketones http://purl.obolibrary.org/obo/RXNO_0000344 alkene oxidative cleavage An alkene oxidation process where the reactant is a quaternary alkene and the products are the corresponding ketones. http://purl.obolibrary.org/obo/MOP_0000589 hydrogenation http://purl.obolibrary.org/obo/MOP_0000569 reduction A reduction process that involves addition of hydrogen atoms across a double bond. http://purl.obolibrary.org/obo/MOP_0000596 pseudohalogenation http://purl.obolibrary.org/obo/MOP_0000566 formation of covalent bond with group Formation of a covalent bond between a substrate and a pseudohalo group. http://purl.obolibrary.org/obo/MOP_0000618 solvolysis http://purl.obolibrary.org/obo/MOP_0000543 molecular process A molecular process where a molecule is broken up by reaction with a molecule that is part of the solvent material. It may be the primary constituent molecule of the solvent material (for example water, ethanol, ammonia) or its lyonium ion or lyate ion. http://purl.obolibrary.org/obo/MOP_0000619 hydrolysis http://purl.obolibrary.org/obo/MOP_0000618 solvolysis A solvolysis reaction where the solvent material is water. http://purl.obolibrary.org/obo/MOP_0000627 condensation reaction http://purl.obolibrary.org/obo/MOP_0000543 molecular process A reaction in which two or more reactants or remote reactive sites within the same molecular entity yield a single main product with accompanying formation of a small molecule. http://purl.obolibrary.org/obo/MOP_0000628 molecular dehydration reaction http://purl.obolibrary.org/obo/MOP_0000627 condensation reaction A condensation reaction where the small molecule produced is water. http://purl.obolibrary.org/obo/MOP_0000642 addition reaction http://purl.obolibrary.org/obo/MOP_0000543 molecular process A reaction of two or more reacting molecular entities resulting in a single reaction product containing all atoms of all components with formation of two chemical bonds and a net reduction in bond multiplicity. http://purl.obolibrary.org/obo/MOP_0000650 amination http://purl.obolibrary.org/obo/MOP_0000802 formation of covalent bond with nitrogen centre Formation of a covalent bond between a substrate and an amino group. http://purl.obolibrary.org/obo/MOP_0000656 elimination reaction http://purl.obolibrary.org/obo/MOP_0000543 molecular process A molecular process where two groups are lost with concomitant formation of an unsaturation in the molecule or formation of a new ring. http://purl.obolibrary.org/obo/MOP_0000671 epoxidation http://purl.obolibrary.org/obo/MOP_0000561 cyclization A cyclisation that results in the formation of an epoxide. http://purl.obolibrary.org/obo/MOP_0000705 oxidation at sulfur http://purl.obolibrary.org/obo/MOP_0000568 oxidation An oxidation process where the oxidation state of at least one sulfur atom increases. http://purl.obolibrary.org/obo/MOP_0000706 oxidation at nitrogen http://purl.obolibrary.org/obo/MOP_0000568 oxidation An oxidation process where the oxidation state of at least one nitrogen atom increases. http://purl.obolibrary.org/obo/MOP_0000712 oxidation state http://purl.obolibrary.org/obo/IAO_0000030 information content entity A formal account of the degree of oxidation of an atom. http://purl.obolibrary.org/obo/MOP_0000713 carboxylation http://purl.obolibrary.org/obo/MOP_0000479 acylation Formation of a covalent bond between a molecule and a carboxy group. http://purl.obolibrary.org/obo/MOP_0000740 acid catalysis http://purl.obolibrary.org/obo/MOP_0000543 molecular process Catalysis of a reaction where the catalyst either donates a hydron or accepts an electron pair. http://purl.obolibrary.org/obo/MOP_0000790 substitution reaction http://purl.obolibrary.org/obo/MOP_0000543 molecular process A reaction in which one singly-bonded group, but not the hydrogen atom, is replaced by another singly-bonded group. http://purl.obolibrary.org/obo/MOP_0000791 aromatic substitution http://purl.obolibrary.org/obo/MOP_0000790 substitution reaction A substitution reaction in which one singly-bonded substituent on an aromatic skeleton is replaced by another singly-bonded substituent. http://purl.obolibrary.org/obo/MOP_0000792 allylic rearrangement http://purl.obolibrary.org/obo/MOP_0000790 substitution reaction A substitution reaction in an allylic system with concomitant migration of the allyl double bond. http://purl.obolibrary.org/obo/MOP_0000793 N-substitution http://purl.obolibrary.org/obo/MOP_0000790 substitution reaction A substitution reaction where the reactive centre is a nitrogen atom. http://purl.obolibrary.org/obo/MOP_0000794 O-substitution http://purl.obolibrary.org/obo/MOP_0000790 substitution reaction A substitution reaction where the reactive centre is an oxygen atom. http://purl.obolibrary.org/obo/MOP_0000795 S-substitution http://purl.obolibrary.org/obo/MOP_0000790 substitution reaction A substitution reaction where the reactive centre is a sulfur atom. http://purl.obolibrary.org/obo/MOP_0000802 formation of covalent bond with nitrogen centre http://purl.obolibrary.org/obo/MOP_0000566 formation of covalent bond with group Formation of a covalent bond with a group where the free valence is on a nitrogen centre. http://purl.obolibrary.org/obo/MOP_0001458 deorganylation http://purl.obolibrary.org/obo/MOP_0000567 breaking of covalent bond with group Breaking of a covalent bond between a substrate and an organyl group. http://purl.obolibrary.org/obo/MOP_0001550 dehalogenation http://purl.obolibrary.org/obo/MOP_0000567 breaking of covalent bond with group Breaking of a covalent bond between a substrate and a halo group. http://purl.obolibrary.org/obo/MOP_0002364 N-methylation http://purl.obolibrary.org/obo/MOP_0000364 methylation Formation of a covalent bond between a nitrogen atom in a substrate and a methyl group. http://purl.obolibrary.org/obo/MOP_0002369 N-alkylation http://purl.obolibrary.org/obo/MOP_0000369 alkylation Formation of a covalent bond between a nitrogen atom in a substrate and an alkyl group. http://purl.obolibrary.org/obo/MOP_0002411 N-arylation http://purl.obolibrary.org/obo/MOP_0000411 arylation Formation of a covalent bond between a nitrogen atom in a substrate and an aryl group. http://purl.obolibrary.org/obo/MOP_0002479 N-acylation http://purl.obolibrary.org/obo/MOP_0000479 acylation Formation of a covalent bond between a nitrogen atom in a substrate and an acyl group. http://purl.obolibrary.org/obo/MOP_0002524 N-sulfonylation http://purl.obolibrary.org/obo/MOP_0000539 sulfonylation Formation of a covalent bond between a nitrogen atom in a substrate and a sulfonyl group. http://purl.obolibrary.org/obo/MOP_0003339 O-silylation http://purl.obolibrary.org/obo/MOP_0000339 silylation Formation of a covalent bond between an oxygen atom in a substrate and a silyl group. http://purl.obolibrary.org/obo/MOP_0003479 O-acylation http://purl.obolibrary.org/obo/MOP_0000479 acylation Formation of a covalent bond between an oxygen atom in a substrate and an acyl group. http://purl.obolibrary.org/obo/MOP_0003524 O-sulfonylation http://purl.obolibrary.org/obo/MOP_0000539 sulfonylation Formation of a covalent bond between an oxygen atom in a substrate and a sulfonyl group. http://purl.obolibrary.org/obo/RXNO_0000383 thiol-yne reaction http://purl.obolibrary.org/obo/RXNO_0000000 molecular skeleton joining reaction Reaction of an thiol with an alkyne to form an alkenyl sulfide. http://purl.obolibrary.org/obo/RXNO_0000660 Corey-Winter elimination http://purl.obolibrary.org/obo/RXNO_0000123 molecular skeleton elimination reaction A chemical reaction for the stereoselective synthesis of an olefin from a 1,2-diol. http://purl.obolibrary.org/obo/RXNO_0000460 intramolecular acyloin condensation http://purl.obolibrary.org/obo/RXNO_0000085 acyloin condensation A reductive coupling reaction between two ester groups in the same molecule to give an acyloin (an alpha-hydroxyketone). http://purl.obolibrary.org/obo/RXNO_0000656 Diimide reduction http://purl.obolibrary.org/obo/MOP_0000642 addition reaction Reductions with diimide are a chemical reactions that convert unsaturated organic compounds to reduced alkane products. In the process, diimide is oxidized to dinitrogen. http://purl.obolibrary.org/obo/RXNO_0000659 Miyaura borylation http://purl.obolibrary.org/obo/RXNO_0000000 molecular skeleton joining reaction A chemical reaction that allows the generation of boronates from vinyl or aryl halides with the cross-coupling of bis(pinacolato)diboron under basic conditions. http://purl.obolibrary.org/obo/RXNO_0000649 Lemieux-Johnson oxidation http://purl.obolibrary.org/obo/RXNO_0000344 alkene oxidative cleavage A cleaving reaction where an olefin is dihydroxylated with osmium tetroxide and undergoes a Malaprade reaction to yield two aldehydes, two ketones, or an aldehyde and a ketone. http://purl.obolibrary.org/obo/RXNO_0000650 Malaprade reaction http://purl.obolibrary.org/obo/RXNO_0000344 alkene oxidative cleavage A cleaving reaction of a 1,2-diol using periodic acid to give the corresponding carbonyl compounds. http://purl.obolibrary.org/obo/RXNO_0000651 Fenton 1,2-glycol oxidation http://purl.obolibrary.org/obo/RXNO_0000012 functional group oxidation The oxidation of a 1,2-glycol with Fenton's reagent (hydrogen peroxide and iron salts) to give an alpha-hydroxy aldehyde. http://purl.obolibrary.org/obo/RXNO_0000652 Fenton alpha-hydroxy carboxylic acid oxidation http://purl.obolibrary.org/obo/RXNO_0000012 functional group oxidation The oxidation of an alpha-hydroxy carboxylic acid with Fenton's reagent to give an alpha-keto carboxylic acid. http://purl.obolibrary.org/obo/RXNO_0000653 Fenton hydrogen peroxide reduction http://purl.obolibrary.org/obo/RXNO_0000012 functional group oxidation The reaction of the components of Fenton's reagent, viz. reduction of hydrogen peroxide by Fe(II) , producing an hydroxyl radical. http://purl.obolibrary.org/obo/RXNO_0000654 Mukaiyama hydration http://purl.obolibrary.org/obo/MOP_0000642 addition reaction The Mukaiyama hydration is an organic reaction involving formal addition of an equivalent of water across an alkene by the action of catalytic bis(acetylacetonato)cobalt(II) complex, phenylsilane and atmospheric oxygen. http://purl.obolibrary.org/obo/CHEBI_32876 tertiary amine http://purl.obolibrary.org/obo/CHEBI_32952 amine http://purl.obolibrary.org/obo/CHEBI_32877 primary amine http://purl.obolibrary.org/obo/CHEBI_32952 amine http://purl.obolibrary.org/obo/CHEBI_32863 secondary amine http://purl.obolibrary.org/obo/CHEBI_32952 amine http://purl.obolibrary.org/obo/CHEBI_33823 enol http://purl.obolibrary.org/obo/CHEBI_33822 organic hydroxy compound http://purl.obolibrary.org/obo/CHEBI_30879 alcohol http://purl.obolibrary.org/obo/CHEBI_33822 organic hydroxy compound http://purl.obolibrary.org/obo/CHEBI_33853 phenols http://purl.obolibrary.org/obo/CHEBI_33659 organic aromatic compound http://purl.obolibrary.org/obo/CHEBI_22213 acridines http://purl.obolibrary.org/obo/CHEBI_35293 fused compound http://purl.obolibrary.org/obo/CHEBI_26455 pyrroles http://purl.obolibrary.org/obo/CHEBI_38101 organonitrogen heterocyclic compound http://purl.obolibrary.org/obo/CHEBI_26513 quinolines http://purl.obolibrary.org/obo/CHEBI_38101 organonitrogen heterocyclic compound http://purl.obolibrary.org/obo/CHEBI_35689 tetrazoles http://purl.obolibrary.org/obo/CHEBI_38101 organonitrogen heterocyclic compound http://purl.obolibrary.org/obo/CHEBI_50075 dihydropyridine http://purl.obolibrary.org/obo/CHEBI_38101 organonitrogen heterocyclic compound http://purl.obolibrary.org/obo/CHEBI_26588 triazines http://purl.obolibrary.org/obo/CHEBI_38101 organonitrogen heterocyclic compound http://purl.obolibrary.org/obo/CHEBI_24828 indoles http://purl.obolibrary.org/obo/CHEBI_35293 fused compound http://purl.obolibrary.org/obo/CHEBI_26410 pyrazoles http://purl.obolibrary.org/obo/CHEBI_38101 organonitrogen heterocyclic compound http://purl.obolibrary.org/obo/CHEBI_26421 pyridines http://purl.obolibrary.org/obo/CHEBI_38101 organonitrogen heterocyclic compound http://purl.obolibrary.org/obo/CHEBI_39447 pyrimidines http://purl.obolibrary.org/obo/CHEBI_38101 organonitrogen heterocyclic compound http://purl.obolibrary.org/obo/CHEBI_48513 carbazoles http://purl.obolibrary.org/obo/CHEBI_35293 fused compound http://purl.obolibrary.org/obo/CHEBI_26961 thiophenes http://purl.obolibrary.org/obo/CHEBI_38106 organosulfur heterocyclic compound http://purl.obolibrary.org/obo/CHEBI_38106 organosulfur heterocyclic compound http://purl.obolibrary.org/obo/CHEBI_5686 heterocyclic compound http://purl.obolibrary.org/obo/CHEBI_38104 oxacycle http://purl.obolibrary.org/obo/CHEBI_5686 heterocyclic compound http://purl.obolibrary.org/obo/CHEBI_17087 ketone http://purl.obolibrary.org/obo/CHEBI_36587 carbonyl compound http://purl.obolibrary.org/obo/CHEBI_33308 carboxylic ester http://purl.obolibrary.org/obo/CHEBI_36587 carbonyl compound http://purl.obolibrary.org/obo/CHEBI_33575 carboxylic acid http://purl.obolibrary.org/obo/CHEBI_36587 carbonyl compound http://purl.obolibrary.org/obo/CHEBI_52094 peroxy acid http://purl.obolibrary.org/obo/CHEBI_36587 carbonyl compound http://purl.obolibrary.org/obo/CHEBI_17478 aldehyde http://purl.obolibrary.org/obo/CHEBI_36587 carbonyl compound http://purl.obolibrary.org/obo/CHEBI_35562 1,2,3-triazole http://purl.obolibrary.org/obo/CHEBI_38597 triazole http://purl.obolibrary.org/obo/CHEBI_27385 tetrachloromethane http://purl.obolibrary.org/obo/CHEBI_23128 chloroalkane http://purl.obolibrary.org/obo/CHEBI_35255 chloroform http://purl.obolibrary.org/obo/CHEBI_23128 chloroalkane http://purl.obolibrary.org/obo/CHEBI_22715 benzimidazoles http://purl.obolibrary.org/obo/CHEBI_23367 molecular entity http://purl.obolibrary.org/obo/CHEBI_25996 phenylhydrazine http://purl.obolibrary.org/obo/CHEBI_23367 molecular entity http://purl.obolibrary.org/obo/CHEBI_33822 organic hydroxy compound http://purl.obolibrary.org/obo/CHEBI_23367 molecular entity http://purl.obolibrary.org/obo/CHEBI_35715 nitro compound http://purl.obolibrary.org/obo/CHEBI_23367 molecular entity http://purl.obolibrary.org/obo/CHEBI_36587 carbonyl compound http://purl.obolibrary.org/obo/CHEBI_23367 molecular entity http://purl.obolibrary.org/obo/CHEBI_25710 organophosphorus compound http://purl.obolibrary.org/obo/CHEBI_23367 molecular entity http://purl.obolibrary.org/obo/CHEBI_25717 organotin compound http://purl.obolibrary.org/obo/CHEBI_23367 molecular entity http://purl.obolibrary.org/obo/CHEBI_32988 amide http://purl.obolibrary.org/obo/CHEBI_23367 molecular entity http://purl.obolibrary.org/obo/CHEBI_37602 allenes http://purl.obolibrary.org/obo/CHEBI_23367 molecular entity http://purl.obolibrary.org/obo/CHEBI_59831 enyne http://purl.obolibrary.org/obo/CHEBI_23367 molecular entity http://purl.obolibrary.org/obo/CHEBI_38269 boronic acids http://purl.obolibrary.org/obo/CHEBI_23367 molecular entity http://purl.obolibrary.org/obo/CHEBI_49553 copper(II) chloride http://purl.obolibrary.org/obo/CHEBI_23367 molecular entity http://purl.obolibrary.org/obo/CHEBI_23252 cinnamic acids http://purl.obolibrary.org/obo/CHEBI_23367 molecular entity http://purl.obolibrary.org/obo/CHEBI_16240 hydrogen peroxide http://purl.obolibrary.org/obo/CHEBI_23367 molecular entity http://purl.obolibrary.org/obo/CHEBI_18140 hydrogen halide http://purl.obolibrary.org/obo/CHEBI_23367 molecular entity http://purl.obolibrary.org/obo/CHEBI_51154 phosphonium ylide http://purl.obolibrary.org/obo/CHEBI_23367 molecular entity http://purl.obolibrary.org/obo/CHEBI_72695 organic molecule http://purl.obolibrary.org/obo/CHEBI_23367 molecular entity http://purl.obolibrary.org/obo/CHEBI_29224 dibromine http://purl.obolibrary.org/obo/CHEBI_23367 molecular entity http://purl.obolibrary.org/obo/CHEBI_30096 diazene http://purl.obolibrary.org/obo/CHEBI_23367 molecular entity http://purl.obolibrary.org/obo/CHEBI_22680 azide http://purl.obolibrary.org/obo/CHEBI_23367 molecular entity http://purl.obolibrary.org/obo/CHEBI_35352 organonitrogen compound http://purl.obolibrary.org/obo/CHEBI_23367 molecular entity http://purl.obolibrary.org/obo/CHEBI_36963 organooxygen compound http://purl.obolibrary.org/obo/CHEBI_23367 molecular entity http://purl.obolibrary.org/obo/CHEBI_25750 oxime http://purl.obolibrary.org/obo/CHEBI_23367 molecular entity http://purl.obolibrary.org/obo/CHEBI_33839 macromolecule http://purl.obolibrary.org/obo/CHEBI_23367 molecular entity http://purl.obolibrary.org/obo/CHEBI_35403 chromium coordination entity http://purl.obolibrary.org/obo/CHEBI_23367 molecular entity http://purl.obolibrary.org/obo/CHEBI_35886 tertiary phosphine http://purl.obolibrary.org/obo/CHEBI_23367 molecular entity http://purl.obolibrary.org/obo/CHEBI_33595 cyclic compound http://purl.obolibrary.org/obo/CHEBI_23367 molecular entity http://purl.obolibrary.org/obo/CHEBI_33641 olefin http://purl.obolibrary.org/obo/CHEBI_23367 molecular entity http://purl.obolibrary.org/obo/CHEBI_51929 arylacetylene http://purl.obolibrary.org/obo/CHEBI_23367 molecular entity http://purl.obolibrary.org/obo/CHEBI_15379 dioxygen http://purl.obolibrary.org/obo/CHEBI_23367 molecular entity http://purl.obolibrary.org/obo/CHEBI_23086 chalcones http://purl.obolibrary.org/obo/CHEBI_23367 molecular entity http://purl.obolibrary.org/obo/CHEBI_278547 sodium azide http://purl.obolibrary.org/obo/CHEBI_23367 molecular entity http://purl.obolibrary.org/obo/CHEBI_35636 carboximides http://purl.obolibrary.org/obo/CHEBI_23367 molecular entity http://purl.obolibrary.org/obo/CHEBI_36601 triphenylphosphane oxide http://purl.obolibrary.org/obo/CHEBI_23367 molecular entity http://purl.obolibrary.org/obo/CHEBI_36605 phthalic anhydride http://purl.obolibrary.org/obo/CHEBI_23367 molecular entity http://purl.obolibrary.org/obo/CHEBI_36606 acid anhydride http://purl.obolibrary.org/obo/CHEBI_23367 molecular entity http://purl.obolibrary.org/obo/CHEBI_59656 phosphine oxide http://purl.obolibrary.org/obo/CHEBI_23367 molecular entity http://purl.obolibrary.org/obo/CHEBI_53434 palladium(II) chloride http://purl.obolibrary.org/obo/CHEBI_23367 molecular entity http://purl.obolibrary.org/obo/CHEBI_23367 molecular entity http://purl.obolibrary.org/obo/CHEBI_24431 chemical entity http://purl.obolibrary.org/obo/CHEBI_33250 atom http://purl.obolibrary.org/obo/CHEBI_24431 chemical entity http://purl.obolibrary.org/obo/CHEBI_24433 group http://purl.obolibrary.org/obo/CHEBI_24431 chemical entity http://purl.obolibrary.org/obo/CHEBI_24469 haloalkane http://purl.obolibrary.org/obo/CHEBI_24472 halohydrocarbon http://purl.obolibrary.org/obo/CHEBI_37592 organic phosphonate http://purl.obolibrary.org/obo/CHEBI_25710 organophosphorus compound http://purl.obolibrary.org/obo/CHEBI_25703 organic phosphate http://purl.obolibrary.org/obo/CHEBI_25710 organophosphorus compound http://purl.obolibrary.org/obo/CHEBI_36871 inorganic radical http://purl.obolibrary.org/obo/CHEBI_26519 radical http://purl.obolibrary.org/obo/CHEBI_36872 organic radical http://purl.obolibrary.org/obo/CHEBI_26519 radical http://purl.obolibrary.org/obo/CHEBI_33256 primary amide http://purl.obolibrary.org/obo/CHEBI_32988 amide http://purl.obolibrary.org/obo/CHEBI_28659 phosphorus atom http://purl.obolibrary.org/obo/CHEBI_33250 atom http://purl.obolibrary.org/obo/CHEBI_33521 metal atom http://purl.obolibrary.org/obo/CHEBI_33250 atom http://purl.obolibrary.org/obo/CHEBI_33403 elemental sulfur http://purl.obolibrary.org/obo/CHEBI_33259 elemental molecular entity http://purl.obolibrary.org/obo/CHEBI_33434 elemental halogen http://purl.obolibrary.org/obo/CHEBI_33259 elemental molecular entity http://purl.obolibrary.org/obo/CHEBI_26708 sodium atom http://purl.obolibrary.org/obo/CHEBI_33521 metal atom http://purl.obolibrary.org/obo/CHEBI_27081 transition element atom http://purl.obolibrary.org/obo/CHEBI_33521 metal atom http://purl.obolibrary.org/obo/CHEBI_37613 cyclohexadiene http://purl.obolibrary.org/obo/CHEBI_33641 olefin http://purl.obolibrary.org/obo/CHEBI_51454 cyclopropanes http://purl.obolibrary.org/obo/CHEBI_33598 carbocyclic compound http://purl.obolibrary.org/obo/OBI_0000011 planned process http://purl.obolibrary.org/obo/BFO_0000015 process http://purl.obolibrary.org/obo/CHEBI_39141 Brønsted acid http://purl.obolibrary.org/obo/BFO_0000016 disposition http://purl.obolibrary.org/obo/CHEBI_39142 Brønsted base http://purl.obolibrary.org/obo/BFO_0000016 disposition http://purl.obolibrary.org/obo/CHEBI_39144 Lewis base http://purl.obolibrary.org/obo/BFO_0000016 disposition http://purl.obolibrary.org/obo/CHEBI_39143 Lewis acid http://purl.obolibrary.org/obo/BFO_0000016 disposition http://purl.obolibrary.org/obo/IAO_0000005 objective specification http://purl.obolibrary.org/obo/IAO_0000030 information content entity http://purl.obolibrary.org/obo/CHEBI_32952 amine http://purl.obolibrary.org/obo/CHEBI_50047 organic amino compound http://purl.obolibrary.org/obo/CHEBI_33860 aromatic amine http://purl.obolibrary.org/obo/CHEBI_33659 organic aromatic compound http://purl.obolibrary.org/obo/CHEBI_17883 hydrogen chloride http://purl.obolibrary.org/obo/CHEBI_18140 hydrogen halide http://purl.obolibrary.org/obo/CHEBI_47266 hydrogen bromide http://purl.obolibrary.org/obo/CHEBI_18140 hydrogen halide http://purl.obolibrary.org/obo/CHEBI_47875 tetrabromomethane http://purl.obolibrary.org/obo/CHEBI_22929 bromoalkane http://purl.obolibrary.org/obo/CHEBI_23019 carbonyl group http://purl.obolibrary.org/obo/CHEBI_24433 group http://purl.obolibrary.org/obo/CHEBI_43176 hydroxy group http://purl.obolibrary.org/obo/CHEBI_24433 group http://purl.obolibrary.org/obo/CHEBI_46883 carboxy group http://purl.obolibrary.org/obo/CHEBI_24433 group http://purl.obolibrary.org/obo/CHEBI_29785 nitro group http://purl.obolibrary.org/obo/CHEBI_24433 group http://purl.obolibrary.org/obo/CHEBI_33338 aryl group http://purl.obolibrary.org/obo/CHEBI_24433 group http://purl.obolibrary.org/obo/CHEBI_36823 pseudohalo group http://purl.obolibrary.org/obo/CHEBI_24433 group http://purl.obolibrary.org/obo/CHEBI_42485 formyl group http://purl.obolibrary.org/obo/CHEBI_24433 group http://purl.obolibrary.org/obo/CHEBI_51142 amino groups http://purl.obolibrary.org/obo/CHEBI_24433 group http://purl.obolibrary.org/obo/CHEBI_26878 tertiary alcohol http://purl.obolibrary.org/obo/CHEBI_30879 alcohol http://purl.obolibrary.org/obo/CHEBI_35681 secondary alcohol http://purl.obolibrary.org/obo/CHEBI_30879 alcohol http://purl.obolibrary.org/obo/CHEBI_15734 primary alcohol http://purl.obolibrary.org/obo/CHEBI_30879 alcohol http://purl.obolibrary.org/obo/CHEBI_33658 arene http://purl.obolibrary.org/obo/CHEBI_33659 organic aromatic compound http://purl.obolibrary.org/obo/CHEBI_33836 benzenoid aromatic compound http://purl.obolibrary.org/obo/CHEBI_33659 organic aromatic compound http://purl.obolibrary.org/obo/CHEBI_73474 acetylenic compound http://purl.obolibrary.org/obo/CHEBI_72695 organic molecule http://purl.obolibrary.org/obo/CHEBI_51849 beta-ketoester http://purl.obolibrary.org/obo/CHEBI_33308 carboxylic ester http://purl.obolibrary.org/obo/CHEBI_51721 alpha,beta-unsaturated ketone http://purl.obolibrary.org/obo/CHEBI_17087 ketone http://purl.obolibrary.org/obo/CHEBI_27539 isatin http://purl.obolibrary.org/obo/CHEBI_24828 indoles http://purl.obolibrary.org/obo/CHEBI_16227 pyridine http://purl.obolibrary.org/obo/CHEBI_26421 pyridines http://purl.obolibrary.org/obo/CHEBI_13759 alkylamine http://purl.obolibrary.org/obo/CHEBI_32877 primary amine http://purl.obolibrary.org/obo/CHEBI_50784 pivalate ester http://purl.obolibrary.org/obo/CHEBI_33308 carboxylic ester http://purl.obolibrary.org/obo/CHEBI_32816 pyruvic acid http://purl.obolibrary.org/obo/CHEBI_33860 aromatic amine http://purl.obolibrary.org/obo/CHEBI_38597 triazole http://purl.obolibrary.org/obo/CHEBI_35352 organonitrogen compound http://purl.obolibrary.org/obo/CHEBI_53212 isocyanates http://purl.obolibrary.org/obo/CHEBI_36963 organooxygen compound http://purl.obolibrary.org/obo/CHEBI_25698 ether http://purl.obolibrary.org/obo/CHEBI_36963 organooxygen compound http://purl.obolibrary.org/obo/CHEBI_51080 nitrate ester http://purl.obolibrary.org/obo/CHEBI_36963 organooxygen compound http://purl.obolibrary.org/obo/CHEBI_23014 carbon oxide http://purl.obolibrary.org/obo/CHEBI_36963 organooxygen compound http://purl.obolibrary.org/obo/CHEBI_16670 peptide http://purl.obolibrary.org/obo/CHEBI_37622 carboxamide http://purl.obolibrary.org/obo/CHEBI_24129 furans http://purl.obolibrary.org/obo/CHEBI_38104 oxacycle http://purl.obolibrary.org/obo/CHEBI_25000 lactone http://purl.obolibrary.org/obo/CHEBI_38104 oxacycle http://purl.obolibrary.org/obo/CHEBI_28802 flavonols http://purl.obolibrary.org/obo/CHEBI_38104 oxacycle http://purl.obolibrary.org/obo/CHEBI_24043 flavones http://purl.obolibrary.org/obo/CHEBI_38104 oxacycle http://purl.obolibrary.org/obo/CHEBI_26407 pyrans http://purl.obolibrary.org/obo/CHEBI_38104 oxacycle http://purl.obolibrary.org/obo/CHEBI_32955 epoxide http://purl.obolibrary.org/obo/CHEBI_38104 oxacycle http://purl.obolibrary.org/obo/CHEBI_38784 oxetanes http://purl.obolibrary.org/obo/CHEBI_38104 oxacycle http://purl.obolibrary.org/obo/CHEBI_38757 isoflavones http://purl.obolibrary.org/obo/CHEBI_38104 oxacycle http://purl.obolibrary.org/obo/CHEBI_73477 terminal acetylenic compound http://purl.obolibrary.org/obo/CHEBI_73474 acetylenic compound http://purl.obolibrary.org/obo/CHEBI_33659 organic aromatic compound http://purl.obolibrary.org/obo/CHEBI_33655 aromatic compound http://purl.obolibrary.org/obo/CHEBI_16648 dialkyl phosphate http://purl.obolibrary.org/obo/CHEBI_22324 alkyl phosphate http://purl.obolibrary.org/obo/CHEBI_16526 carbon dioxide http://purl.obolibrary.org/obo/CHEBI_23014 carbon oxide http://purl.obolibrary.org/obo/CHEBI_22324 alkyl phosphate http://purl.obolibrary.org/obo/CHEBI_25703 organic phosphate http://purl.obolibrary.org/obo/CHEBI_37622 carboxamide http://purl.obolibrary.org/obo/CHEBI_33256 primary amide http://purl.obolibrary.org/obo/CHEBI_18379 nitrile http://purl.obolibrary.org/obo/CHEBI_23424 cyanides http://purl.obolibrary.org/obo/CHEBI_23128 chloroalkane http://purl.obolibrary.org/obo/CHEBI_24469 haloalkane http://purl.obolibrary.org/obo/CHEBI_37757 iodoalkane http://purl.obolibrary.org/obo/CHEBI_24469 haloalkane http://purl.obolibrary.org/obo/CHEBI_22929 bromoalkane http://purl.obolibrary.org/obo/CHEBI_24469 haloalkane http://purl.obolibrary.org/obo/CHEBI_37579 acyl halide http://purl.obolibrary.org/obo/CHEBI_37578 halide http://purl.obolibrary.org/obo/CHEBI_48420 chromium trioxide http://purl.obolibrary.org/obo/CHEBI_35403 chromium coordination entity http://purl.obolibrary.org/obo/CHEBI_5686 heterocyclic compound http://purl.obolibrary.org/obo/CHEBI_33595 cyclic compound http://purl.obolibrary.org/obo/CHEBI_33635 polycyclic compound http://purl.obolibrary.org/obo/CHEBI_33595 cyclic compound http://purl.obolibrary.org/obo/CHEBI_35293 fused compound http://purl.obolibrary.org/obo/CHEBI_33635 polycyclic compound http://purl.obolibrary.org/obo/CHEBI_32878 alkene http://purl.obolibrary.org/obo/CHEBI_33641 olefin http://purl.obolibrary.org/obo/CHEBI_38166 organic heteropolycyclic compound http://purl.obolibrary.org/obo/CHEBI_33671 heteropolycyclic compound http://purl.obolibrary.org/obo/CHEBI_46882 amino group http://purl.obolibrary.org/obo/CHEBI_51142 amino groups http://purl.obolibrary.org/obo/CHEBI_51236 organomagnesium halide http://purl.obolibrary.org/obo/CHEBI_51187 organomagnesium compound http://purl.obolibrary.org/obo/CHEBI_55380 beta-hydroxy ketone http://purl.obolibrary.org/obo/CHEBI_52395 oxyketone http://purl.obolibrary.org/obo/CHEBI_50413 hydroxyaldehyde http://purl.obolibrary.org/obo/CHEBI_17478 aldehyde http://purl.obolibrary.org/obo/CHEBI_16842 formaldehyde http://purl.obolibrary.org/obo/CHEBI_17478 aldehyde http://purl.obolibrary.org/obo/CHEBI_22698 benzaldehydes http://purl.obolibrary.org/obo/CHEBI_17478 aldehyde http://purl.obolibrary.org/obo/CHEBI_22495 arenecarbaldehyde http://purl.obolibrary.org/obo/CHEBI_17478 aldehyde http://purl.obolibrary.org/obo/CHEBI_28112 nickel atom http://purl.obolibrary.org/obo/CHEBI_27081 transition element atom http://purl.obolibrary.org/obo/CHEBI_28694 copper atom http://purl.obolibrary.org/obo/CHEBI_27081 transition element atom http://purl.obolibrary.org/obo/CHEBI_33341 titanium atom http://purl.obolibrary.org/obo/CHEBI_27081 transition element atom http://purl.obolibrary.org/obo/CHEBI_33363 palladium atom http://purl.obolibrary.org/obo/CHEBI_27081 transition element atom http://purl.obolibrary.org/obo/CHEBI_33364 platinum atom http://purl.obolibrary.org/obo/CHEBI_27081 transition element atom http://purl.obolibrary.org/obo/CHEBI_27363 zinc atom http://purl.obolibrary.org/obo/CHEBI_27081 transition element atom http://purl.obolibrary.org/obo/CHEBI_24079 formamides http://purl.obolibrary.org/obo/CHEBI_35636 carboximides http://purl.obolibrary.org/obo/CHEBI_35873 carboxylic anhydride http://purl.obolibrary.org/obo/CHEBI_36606 acid anhydride http://purl.obolibrary.org/obo/CHEBI_36687 acyl chloride http://purl.obolibrary.org/obo/CHEBI_37579 acyl halide http://purl.obolibrary.org/obo/CHEBI_50888 fluoroarene http://purl.obolibrary.org/obo/CHEBI_50887 haloarene http://purl.obolibrary.org/obo/CHEBI_37148 bromoarene http://purl.obolibrary.org/obo/CHEBI_50887 haloarene http://purl.obolibrary.org/obo/MOP_0000364 methylation http://purl.obolibrary.org/obo/MOP_0000369 alkylation http://purl.obolibrary.org/obo/MOP_0000721 [3,3]-sigmatropic rearrangement http://purl.obolibrary.org/obo/MOP_0000543 molecular process http://purl.obolibrary.org/obo/MOP_0000731 base catalysis http://purl.obolibrary.org/obo/MOP_0000543 molecular process http://purl.obolibrary.org/obo/MOP_0000732 hydron donation http://purl.obolibrary.org/obo/MOP_0000543 molecular process http://purl.obolibrary.org/obo/MOP_0000733 accepting an electron pair in Lewis adduct formation http://purl.obolibrary.org/obo/MOP_0000543 molecular process http://purl.obolibrary.org/obo/MOP_0000737 accepting a hydron http://purl.obolibrary.org/obo/MOP_0000543 molecular process http://purl.obolibrary.org/obo/MOP_0000738 electron pair donation in Lewis adduct formation http://purl.obolibrary.org/obo/MOP_0000543 molecular process http://purl.obolibrary.org/obo/MOP_0000739 Lewis adduct formation http://purl.obolibrary.org/obo/MOP_0000543 molecular process http://purl.obolibrary.org/obo/MOP_0000735 Lewis base catalysis http://purl.obolibrary.org/obo/MOP_0000731 base catalysis http://purl.obolibrary.org/obo/MOP_0000736 Brønsted base catalysis http://purl.obolibrary.org/obo/MOP_0000731 base catalysis http://purl.obolibrary.org/obo/MOP_0000730 Brønsted acid catalysis http://purl.obolibrary.org/obo/MOP_0000740 acid catalysis http://purl.obolibrary.org/obo/MOP_0000734 Lewis acid catalysis http://purl.obolibrary.org/obo/MOP_0000740 acid catalysis http://purl.obolibrary.org/obo/RXNO_0000625 obsolete: bromo Heck reaction A Heck reaction where an organobromide couples to a terminal olefin to produce an internal olefin, catalysed by palladium. http://purl.obolibrary.org/obo/RXNO_0000004 obsolete: ring reaction A reaction in which the number of atoms in any ring changes between the reactant and the products. http://purl.obolibrary.org/obo/RXNO_0000024 Heck reaction A carbon-carbon coupling reaction where an organohalide or triflate couples to a terminal olefin to produce an internal olefin, catalysed by palladium. It is stereospecific. http://purl.obolibrary.org/obo/CHEBI_24431 chemical entity http://purl.obolibrary.org/obo/RXNO_0000564 obsolete: acyclic Beckmann rearrangement/Sandmeyer chlorination http://purl.obolibrary.org/obo/RXNO_0000565 obsolete: Baeyer–Emmerling indole synthesis/Sandmeyer bromination http://purl.obolibrary.org/obo/RXNO_0000566 obsolete: bromo Sonogashira coupling/Sandmeyer iodination http://purl.obolibrary.org/obo/RXNO_0000567 obsolete: bromo Suzuki coupling/iodo Heck reaction http://purl.obolibrary.org/obo/RXNO_0000568 obsolete: bromo Suzuki-type coupling/triflyloxy Heck reaction http://purl.obolibrary.org/obo/RXNO_0000569 obsolete: bromolactonization/bromo Heck-type reaction http://purl.obolibrary.org/obo/RXNO_0000570 obsolete: chloro Sonogashira coupling/chloro Heck-type reaction http://purl.obolibrary.org/obo/RXNO_0000571 obsolete: chloro Suzuki coupling/Heck-type reaction http://purl.obolibrary.org/obo/RXNO_0000572 obsolete: chloro Suzuki-type coupling/bromo Heck reaction http://purl.obolibrary.org/obo/RXNO_0000573 obsolete: chlorolactonization/chloro Heck reaction http://purl.obolibrary.org/obo/RXNO_0000596 obsolete: Combes quinoline synthesis/Conrad%E2%80%93Limpach_synthesis http://purl.obolibrary.org/obo/BFO_0000015 process http://purl.obolibrary.org/obo/BFO_0000016 disposition http://purl.obolibrary.org/obo/IAO_0000030 information content entity http://purl.obolibrary.org/obo/RXNO_0000557 obsolete: Heck-type reaction/cross-coupling http://purl.obolibrary.org/obo/RXNO_0000558 obsolete: bromo Heck reaction/Liebeskind-Srogl coupling http://purl.obolibrary.org/obo/RXNO_0000559 obsolete: chloro Heck reaction/Fukuyama coupling http://purl.obolibrary.org/obo/RXNO_0000560 obsolete: iodo Heck reaction/chloride Finkelstein reaction http://purl.obolibrary.org/obo/RXNO_0000561 obsolete: triflyloxy Heck reaction/bromide Finkelstein reaction http://purl.obolibrary.org/obo/RXNO_0000562 obsolete: bromo Heck-type reaction/sulfonate ester Finkelstein reaction http://purl.obolibrary.org/obo/RXNO_0000563 obsolete: chloro Heck-type reaction/Sandmeyer fluorination http://purl.obolibrary.org/obo/RXNO_0000416 protects http://purl.obolibrary.org/obo/BFO_0000078 has participant ceasing to exist The notion here is that a given reaction is meant to 'protect' a given group from reacting in a subsequent process and can be 'deprotected' later. http://purl.obolibrary.org/obo/RXNO_0000417 deprotects http://purl.obolibrary.org/obo/BFO_0000077 has participant beginning to exist If a reaction R deprotects a group G, then G is in the product where it wasn't in the reactant. http://purl.obolibrary.org/obo/RXNO_0000423 has specified product http://purl.obolibrary.org/obo/BFO_0000077 has participant beginning to exist A relation between a planned reaction step and a molecular entity participating in that process. The creation of the molecular entity during the process is explicitly specified in the objective specification which the planned reaction step realizes the concretization of. http://purl.obolibrary.org/obo/RXNO_0000424 has specified reactant http://purl.obolibrary.org/obo/BFO_0000078 has participant ceasing to exist A relation between a planned reaction step and a molecular entity participating in that process that is not created during the process. The destruction of the molecular entity during the process is explicitly specified in the plan specification which the process realizes the concretization of. http://purl.obolibrary.org/obo/RXNO_0000425 has_catalyst http://purl.obolibrary.org/obo/BFO_0000057 has_participant A relation between a planned reaction step and a molecular entity participating in that process that has_role catalyst ((CHEBI:35223). http://purl.obolibrary.org/obo/RXNO_0000469 has_intermediate http://purl.obolibrary.org/obo/BFO_0000057 has_participant A relation between a planned reaction step and a molecular entity participating in that process. The creation and subsequent destruction of the molecular entity during the process are explicitly specified in the plan specification which the process realizes the concretization of. http://purl.obolibrary.org/obo/BFO_0000078 has participant ceasing to exist http://purl.obolibrary.org/obo/BFO_0000057 has_participant http://purl.obolibrary.org/obo/BFO_0000077 has participant beginning to exist http://purl.obolibrary.org/obo/BFO_0000057 has_participant http://purl.obolibrary.org/obo/OBI_0000417 achieves_planned_objective This relation obtains between a planned process and a objective specification when the criteria specified in the objective specification are met at the end of the planned process. http://purl.obolibrary.org/obo/BFO_0000057 has_participant http://purl.obolibrary.org/obo/BFO_0000055 realizes http://purl.obolibrary.org/obo/rxno.obo#has_part has_part http://purl.obolibrary.org/obo/rxno.obo#part_of part_of http://purl.obolibrary.org/obo/BFO_0000162 has disposition at all times