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Clay-Kinnear-Perren Condensation

Published Online: 15 SEP 2010

DOI: 10.1002/9780470638859.conrr147

Comprehensive Organic Name Reactions and Reagents

Comprehensive Organic Name Reactions and Reagents

How to Cite

2010. Clay-Kinnear-Perren Condensation. Comprehensive Organic Name Reactions and Reagents. 147:669–672.

Publication History

  1. Published Online: 15 SEP 2010

Abstract

The synthesis of alkylphosphonic dichlorides from alkyl chlorides, phosphorous trichloride, and aluminum chloride is known as the Clay–Kinnear–Perren condensation. Various factors have been found that cause important effects on this reaction, such as the order of mixing reagents, control of reaction temperature, anhydrous conditions of the reagents and apparatus, and the final molar ratio of water to ionic complex in hydrolysis. However, no rearrangement has been found for the complex from chloromethyltrimethylsilane, even though chloromethyltrimethylsilane undergoes a Wagner–Meerwein rearrangement to chlorodimethylethylsilane when treated with AlCl3; this reaction does not apply to chlorosilane, either.

Keywords:

  • alkylphosphonic dichlorides;
  • alkylphosphonic acids;
  • alkyl chloride;
  • chloromethyltrimethylsilane