Methylthiomethyl Esters (II) Transesterification and Amide Formation

Abstract

Recently the preparation and the hydrolytic properties of methylthiomethyl esters (1) were described.¹ However, the question of whether water attacks the acyl or the alkyl carbon atom during the process of neutral hydrolysis remained unsettled. We now wish to provide evidence in favor of an acyl cleavage pathway, and further outline some synthetic applications of this class of compounds.