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Ketonic decarboxylation (also known as decarboxylative ketonization) is a type of organic reaction and a decarboxylation converting two equivalents of a carboxylic acid (R−C(=O)OH) to a symmetric ketone (R 2 C=O) by the application of heat.
The presence of the keto group at the beta position allows them to easily undergo thermal decarboxylation. [7] Gamma-keto acids, Gamma-ketoacids, or 4-oxoacids have the ketone group at the third carbon from the carboxylic acid. Levulinic acid is an example. Keto acids appear in a wide variety of anabolic pathways in metabolism.
Decarboxylation is one of the oldest known organic reactions. It is one of the processes assumed to accompany pyrolysis and destructive distillation. Overall, decarboxylation depends upon stability of the carbanion synthon R −, [1] [2] although the anion may not be a true chemical intermediate.
By decarboxylation of carboxylic anhydride. Ketones can be prepared from haloketones in reductive dehalogenation of halo ketones. In ketonic decarboxylation symmetrical ketones are prepared from carboxylic acids. [10] [17] Hydrolysis of unsaturated secondary amides, [18] β-Keto acid esters, [10] or β-diketones (the acetoacetic ester synthesis).
Phenylacetic acid undergoes ketonic decarboxylation to form ketones. [7] It can be condensed with itself to form dibenzyl ketone , or with a large excess of another carboxylic acid (in the form of an acid anhydride ), such as with acetic anhydride to form phenylacetone .
This was a result of the fact that any halide anion generated in the reaction inhibited the Cu-catalyzed decarboxylation process. [15] Further optimization of the system and catalyst conditions has made decarboxylative cross-coupling using bimetallic Pd–Cu systems applicable to organic synthesis, most predominantly in the formation of biaryls ...
This enzyme complex catalyzes the oxidative decarboxylation of branched, short-chain alpha-ketoacids. BCKDC is a member of the mitochondrial α-ketoacid dehydrogenase complex family, which also includes pyruvate dehydrogenase and alpha-ketoglutarate dehydrogenase, key enzymes that function in the Krebs cycle.
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 ...