Standard Article

The Wittig Reaction

  1. Adalbert Maercker

Published Online: 15 MAR 2011

DOI: 10.1002/0471264180.or014.03

Organic Reactions

Organic Reactions

How to Cite

Maercker, A. 2011. The Wittig Reaction. Organic Reactions. 14:3:270–490.

Author Information

  1. University of Heidelberg

Publication History

  1. Published Online: 15 MAR 2011

Chemistry Terms

Choose one or more boxes to highlight terms.

Abstract

In 1953 Wittig and Geissler found that reaction of benzophenone with methylenetriphenylphosphorane gave 1,1-diphenylethylene and triphenylphosphine oxide in almost quantitative yield; the phosphine had been prepared from triphenylmethylphosphonium bromide and phenyl lithium. The discovery led to the development of a new method for the synthesis of olefins, under the name Wittig reaction. One advantage of this new method is that the carbonyl group is replaced specifically by a carbon-carbon double bond without the formation of isomeric olefins. In contrast, the older method of converting carbonyl compounds to olefins using the Grignard reaction usually give a mixture of isomeric olefins. Another advantage is the Wittig reaction is carried out under mild conditions. Discussions of modern techniques for the preparation of methylene phosphoranes are included in this review.

Keywords:

  • wittig reaction;
  • alkylidene triphenylphosphoranes;
  • alkyl-substituted olefins;
  • aryl-substituted olefins;
  • unsaturated carbonyl compounds;
  • vinyl halides;
  • vinyl ethers;
  • natural products;
  • side reactions;
  • vitamins;
  • steroids;
  • experimental conditions