Cleavage and Formation of P-C Bonds During an Unusual Kinnear-Perren Reaction

Plack, Volker; Goerlich, Jens R.; Schmutzler, Reinhard

doi:10.1515/znb-1998-1104

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Clay‐Kinnear‐Perren Condensation

2010

Comprehensive Organic Name Reactions and Reagents

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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 AlCl 3 ; this reaction does not apply to chlorosilane, either.

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