Use of acylphosphonates for the synthesis of alpha-chlorinated carboxylic and alpha,alpha'-dichloro dicarboxylic acids and their derivatives

alpha -Chloro acylphosphonates and alpha,alpha'-dichloro bisacylphosphonate s were prepared in situ by chlorination of acylphosphonates and bisacylphos phonates, respectively, using sulfuryl chloride. Subsequently, they were cl eaved to the corresponding alpha -chlorinated or alpha,alpha'-dichlorinated (di)carboxylic acids with a hydrogen peroxide-sodium bicarbonate system. P erforming the cleavage with an alcohol or an amine yielded the correspondin g alpha -chlorinated esters and alpha -chlorinated amides, respectively. (C ) 2001 Elsevier Science Ltd. All rights reserved.