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Favorskii Rearrangement

Published Online: 15 SEP 2010

DOI: 10.1002/9780470638859.conrr224

Comprehensive Organic Name Reactions and Reagents

Comprehensive Organic Name Reactions and Reagents

How to Cite

2010. Favorskii Rearrangement. Comprehensive Organic Name Reactions and Reagents. 224:1026–1031.

Publication History

  1. Published Online: 15 SEP 2010

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Abstract

The Favorskii rearrangement is a base-induced rearrangement of α-halo ketones to the corresponding carboxylic acid derivatives (e.g., acids, esters, and amides) with the same number of carbon atoms in the skeletons; and the bases can be hydroxide, alkoxide, or amines. There have been at least six different mechanisms presented for this rearrangement. Among these mechanisms, the semibenzilic acid mechanism and cyclopropanone mechanisms are most plausible. Besides this, many experimental results have shown that the actual reaction mechanisms depend on the reaction conditions. This reaction has wide application for the synthesis of highly strained esters, bicyclic esters, some steroids, etc.

Keywords:

  • α-halo ketones;
  • epoxide;
  • oxyallylic anion;
  • β-halo ketones