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Krapcho decarboxylation is a chemical reaction used to manipulate certain organic esters. [1] This reaction applies to esters with a beta electron-withdrawing group (EWG) . The reaction proceeds by nucleophilic dealkylation of the ester by the halide followed by decarboxylation, followed by hydrolysis of the resulting stabilized carbanion.
The Barton decarboxylation is an unusual radical reductive decarboxylation. As described above, most decarboxylations start with a carboxylic acid or its alkali metal salt, but the Krapcho decarboxylation starts with methyl esters. In this case, the reaction begins with halide-mediated cleavage of the ester, forming the carboxylate.
Barton decarboxylation; Barton reaction [22] [23] Barton–Kellogg reaction; Barton–McCombie reaction, Barton deoxygenation; Barton-Zard Synthesis; Barton vinyl iodine procedure; Baudisch reaction; Bayer test; Baylis–Hillman reaction; Bechamp reaction; Bechamp reduction; Beckmann fragmentation; Beckmann rearrangement; Bellus–Claisen ...
Highly specialized demethylations are abundant, such as the Krapcho decarboxylation: A mixture of anethole, KOH, and alcohol was heated in an autoclave. Although the product of this reaction was the expected anol, a highly reactive dimerization product in the mother liquors called dianol was also discovered by Charles Dodds.
Moreover, it was shown that olefin generation and the following decarboxylation could be performed in one pot. To that end, excess NaI was added, along with an elevation in temperature to facilitate the Krapcho decarboxylation. [15] [16] Application of the Bamford-Stevens reaction in natural product total synthesis
Studies of decarboxylation over nickel and palladium-based catalysts were first reported by Wilhelm Maier et al., in 1982, [6] when they achieved the deoxygenation of several carboxylic acids via decarboxylation under a hydrogen atmosphere. This included the conversion of aliphatic acids (such as heptanoic and octanoic acids) to alkanes (namely ...
The first reported decarboxylative cross coupling reaction was an Ullmann reaction, in 1966 by Nilsson et al. Thermal decarboxylation of copper benzoates, in the presence of an aryl halide, was found to produce (both symmetric and unsymmetric) biaryls through aryl-Cu intermediates. [2] First reported decarboxylative Ullmann coupling (Nilsson, 2005)
Usually, they are named after the substrate whose decarboxylation they catalyze, for example pyruvate decarboxylase catalyzes the decarboxylation of pyruvate.