Acyl-O versus aryl-O bond scission in reactions of benzenethiolate with nitrophenyl esters of carboxylic acids

Abstract

A number of nitrophenyl esters of carboxylic acids have been found to undergo both carbonyl carbon–oxygen and aryl carbon–oxygen scission in reactions with the benzenethiolate ion in ethanol; the fraction of C_CO–O scission increases with increasing polarity of the medium and varies, according to the ester substrate, from 100% with p-nitrophenyl acetate to 0% with 2,4,6-trintrophenyl benzoate.