Standard Article

Perkow Reaction

Published Online: 15 SEP 2010

DOI: 10.1002/9780470638859.conrr489

Comprehensive Organic Name Reactions and Reagents

Comprehensive Organic Name Reactions and Reagents

How to Cite

2010. Perkow Reaction. Comprehensive Organic Name Reactions and Reagents. 489:2168–2172.

Publication History

  1. Published Online: 15 SEP 2010

Chemistry Terms

Choose one or more boxes to highlight terms.

Abstract

The preparation of vinyl (or enol) phosphates from α-halo carbonyl compounds and trivalent phosphorus reagents and is generally known as the Perkow reaction. The study finds that, α-halo aldehydes are more reactive than α-halo ketones; whereas α-halo esters are the least reactive species for the Perkow reaction, and α-halo amides do not react at all. It has been found that the more α-halo atoms in the carbonyl compound, the faster the reaction occurs. All the suitable reagents have been suggested for this reaction Both the electronic character of phosphorus and the steric effects are prominent in the Perkow reaction, as indicated by the predominant trans-configuration in vinyl phosphates. It is observed that the course of the reaction depends on the nature and position of halogen on the carbonyl compounds as well as the reaction temperature. This reaction has importance for the preparation of vinyl phosphates.

Keywords:

  • α-halo esters;
  • trialkyl phosphites;
  • alkyl halide;
  • α-bromoketone