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Decarboxylation is a chemical reaction that removes a carboxyl group and releases carbon dioxide (CO 2). Usually, decarboxylation refers to a reaction of carboxylic acids , removing a carbon atom from a carbon chain.
Some cyclic molecules containing a ketone undergo a cheletropic extrusion reaction, leaving new carbon–carbon π bonds on the remaining structure. This reaction can be spontaneous, as in the synthesis of hexaphenylbenzene. Cyclopropenones and cyclobutenediones can be converted to alkynes by elimination of one or two molecules of CO ...
Orthoesters can be obtained by the reaction of alcohols under acidic water free conditions with benzonitrile. Reduction to benzaldehyde and benzyl alcohol is possible using DIBAL-H, LiAlH 4 or sodium borohydride. Decarboxylation to benzene may be effected by heating in quinoline in the presence of copper salts.
Another example is the synthesis of 2,7-dimethyl-2,7-dinitrooctane from 4-methyl-4-nitrovaleric acid: [3] The Kolbe reaction has also been occasionally used in cross-coupling reactions . In 2022, it was discovered that the Kolbe electrolysis is enhanced if an alternating square wave current is used instead of a direct current .
Upon heating, 2,4,6-trinitrobenzoic acid undergoes decarboxylation to give 1,3,5-trinitrobenzene. [4] Reduction with tin gives 2,4,6-triaminobenzenoic acid, a precursor to phloroglucinol (1,3,5-trihydroxybenzene).
Trinitrobenzene is more explosive than TNT, but more expensive. [2] It is primarily used as a high explosive compound for commercial mining and military applications. It has also been used as a narrow-range pH indicator, an agent to vulcanize natural rubber, and a mediating agent to mediate the synthesis of other explosive compounds.
Dibenzyl ketone is prepared by ketonic decarboxylation of phenylacetic acid. One method is where phenylacetic acid is reacted with acetic anhydride and anhydrous potassium acetate and refluxed for two hours at 140−150 °C. The mixture is distilled slowly so that the distillate is mostly acetic acid. Carbon dioxide is released in this reaction ...
First performed by Justus von Liebig in 1838, [1] it is the first reported example of a rearrangement reaction. [2] It has become a classic reaction in organic synthesis and has been reviewed many times before. [3] [4] [5] It can be viewed as an intramolecular redox reaction, as one carbon center is oxidized while the other is reduced. Scheme 1.