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homologation reaction wikipedia jump to content main menu main menu move to sidebar hide navigation main page contents current events random article about wikipedia contact us contribute help learn to edit community portal recent changes upload file special pages search search appearance donate create account log in personal tools donate create account log in contents move to sidebar hide top 1 chain reduction 2 see also 3 references toggle the table of contents homologation reaction 7 languages čeština deutsch فارسی français italiano nederlands українська edit links article talk english read edit view history tools tools move to sidebar hide actions read edit view history general what links here related changes upload file permanent link page information cite this page get shortened url switch to legacy parser print export download as pdf printable version in other projects wikidata item appearance move to sidebar hide from wikipedia the free encyclopedia chemical reaction which converts between members of a homologous series in organic chemistry a homologation reaction also known as homologization is any chemical reaction that converts the reactant into the next member of the homologous series a homologous series is a group of compounds that differ by a constant unit generally a methylene ch 2 group the reactants undergo a homologation when the number of a repeated structural unit in the molecules is increased the most common homologation reactions increase the number of methylene ch 2 units in saturated chain within the molecule 1 for example the reaction of aldehydes or ketones with diazomethane or methoxymethylenetriphenylphosphine to give the next homologue in the series examples of homologation reactions include kiliani fischer synthesis where an aldose molecule is elongated through a three step process consisting of nucleophillic addition of cyanide to the carbonyl to form a cyanohydrin hydrolysis to form a lactone reduction to form the homologous aldose wittig reaction of an aldehyde with methoxymethylenetriphenylphosphine which produces a homologous aldehyde arndt eistert reaction is a series of chemical reactions designed to convert a carboxylic acid to a higher carboxylic acid homologue i e contains one additional carbon atom kowalski ester homologation an alternative to the arndt eistert synthesis has been used to convert β amino esters from α amino esters through an ynolate intermediate 2 seyferth gilbert homologation in which an aldehyde is converted to a terminal alkyne and then hydrolyzed back to an aldehyde some reactions increase the chain length by more than one unit for example the demayo reaction can be considered a two carbon homologation reaction chain reduction edit likewise the chain length can also be reduced in the gallagher hollander degradation 1946 pyruvic acid is removed from a linear aliphatic carboxylic acid yielding a new acid with 2 carbon atoms less 3 the original publication concerns the conversion of bile acid in a series of reactions acid chloride 2 formation with thionyl chloride diazoketone formation 3 with diazomethane chloromethyl ketone formation 4 with hydrochloric acid organic reduction of chlorine to methylketone 5 ketone halogenation to 6 elimination reaction with pyridine to enone 7 and finally oxidation with chromium trioxide to bisnorcholanic acid 8 in the hooker reaction 1936 an alkyl chain in a certain naphthoquinone phenomenon first observed in the compound lapachol is reduced by one methylene unit as carbon dioxide in each potassium permanganate oxidation 4 5 mechanistically oxidation causes ring cleavage at the alkene group extrusion of carbon dioxide in decarboxylation with subsequent ring closure see also edit homologous series references edit encyclopedia of inorganic chemistry doi 10 1002 0470862106 id396 d gray c concellon and t gallagher 2004 kowalski ester homologation application to the synthesis of β amino esters j org chem 69 14 4849 4851 doi 10 1021 jo049562h pmid 15230615 vincent p hollander and t f gallagher partial synthesis of compounds related to adrenal cortical hormones vii degradation of the side chain of cholanic acid j biol chem mar 1946 162 549 554 link archived 2009 01 07 at the wayback machine on the oxidation of 2 hydroxy 1 4 naphthoquinone derivatives with alkaline potassium permanganate samuel c hooker j am chem soc 1936 58 7 1174 1179 doi 10 1021 ja01298a030 on the oxidation of 2 hydroxy 1 4 naphthoquinone derivatives with alkaline potassium permanganate part ii compounds with unsaturated side chains samuel c hooker and al steyermark j am chem soc 1936 58 7 pp 1179 1181 doi 10 1021 ja01298a031 retrieved from https en wikipedia org w index php title homologation_reaction oldid 1241099978 categories homologation reactions carbon carbon bond forming reactions hidden categories articles with short description short description is different from wikidata webarchive template wayback links this page was last edited on 19 august 2024 at 09 50 utc page was rendered with parsoid text is available under the creative commons attribution sharealike 4 0 license additional terms may apply by using this site you agree to the terms of use and privacy policy wikipedia is a registered trademark of the wikimedia foundation inc a non profit organization privacy policy about wikipedia disclaimers contact wikipedia legal safety contacts code of conduct developers statistics cookie statement mobile view search search toggle the table of contents homologation reaction 7 languages add topic