Bart Vanderhoydonck

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

Abstract α-Chloro acylphosphonates and α,α′-dichloro bisacylphosphonates were prepared in situ by chlorination of acylphosphonates and bisacylphosphonates, respectively, using sulfuryl chloride. Subsequently, they were cleaved to the corresponding α-chlorinated or α,α′-dichlorinated (di)carboxylic acids with a hydrogen peroxide–sodium bicarbonate system. Performing the cleavage with an alcohol or an amine yielded the corresponding α-chlorinated esters and α-chlorinated amides, respectively.