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Krapcho decarboxylation information


Krapcho decarboxylation
Named after A. Paul Krapcho
Reaction type Substitution reaction
Identifiers
RSC ontology ID RXNO:0000507

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.[2]

ZCH2CO2CH3 + I + H2O → ZCH3 + CH3I + CO2 + OH
  1. ^ Cite error: The named reference :1 was invoked but never defined (see the help page).
  2. ^ Poon, Po. S.; Banerjee, Ajoy K.; Laya, Manuel S. (2011). "Advances in the Krapcho Decarboxylation". Journal of Chemical Research. 35 (2): 67–73. doi:10.3184/174751911X12964930076403. ISSN 1747-5198.

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Krapcho decarboxylation

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Decarboxylation

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The Krapcho decarboxylation is the characteristic halide-mediated decarboxylation of such acids' methyl esters. Those facile decarboxylations are an...

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List of organic reactions

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rearrangement Kostanecki acylation Kowalski ester homologation Krapcho decarboxylation Krische allylation Kröhnke aldehyde synthesis Kröhnke oxidation...

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saponification. Highly specialized demethylations are abundant, such as the Krapcho decarboxylation: A mixture of anethole, KOH, and alcohol was heated in an autoclave...

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Ester

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alkylation. Methyl esters are often susceptible to decarboxylation in the Krapcho decarboxylation. Phenyl esters react to hydroxyarylketones in the Fries...

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