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Kochi Reaction

(Kochi Oxidative Decarboxylation)

Published Online: 15 SEP 2010

DOI: 10.1002/9780470638859.conrr367

Comprehensive Organic Name Reactions and Reagents

Comprehensive Organic Name Reactions and Reagents

How to Cite

2010. Kochi Reaction. Comprehensive Organic Name Reactions and Reagents. 367:1646–1649.

Publication History

  1. Published Online: 15 SEP 2010

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Abstract

The carboxylic acids conversion into corresponding halides via the oxidative degradation of carboxylic acid by lead tetraacetate (LTA) accompanied by a simultaneous replacement with a halogen under free-radical conditions in the presence of a stoichiometric amount of metal halide is referred to as the Kochi reaction. The study represents the oxidation of the carboxylic acid in the absence of the metal halides either thermally or photochemically and shows that the structure of the substrates affects the oxidation outcome, and the relative rates of oxidation by Pb(IV) determine the distribution of products. Several conditions of the reaction have been discussed, which enhance or inhibit the oxidative decarboxylation. This reaction has been modified to occur using different oxidants and generally useful for the preparation of secondary and tertiary halides.

Keywords:

  • carboxylic acids;
  • lead tetraacetate (LTA);
  • acyloxy radical;
  • oxidants