Alkaline hydrolysis of esters possessing readily ionisable amide groups: evidence for the 1→4 migration of an anilino-group in the alkaline reaction of O-aroyl-N-arylglycolamides

Abstract

U.v. scanning experiments indicate the formation of diacylamine intermediates in the alkaline reaction of O-4-nitrobenzoyl- and O-benzoyl-N-nitrophenylglycolamide. The product of these reactions includes the benzanilide derived from a 1→4 migration of the anilino-group. As the electron-withdrawing power of the substituent on the anilino-group decreases the mechanism involving direct hydroxide attack on the acyl group takes the major portion of the reaction flux.