Amidoximes as Effective Acceptors of Acyl Group

A detailed analysis of the kinetic behavior of amidoximes in acyl transfer reactions was undertaken in terms of the Brönsted relationship. The reactivity of amidoximate anions is comparable with the reactivity of typical -nucleophiles (oximate ions). The anomalously high nucleophilicity of neutral amidoximes can be explained by the formation of a cyclic transition state, including two types of promoting action – general acid and base catalysis. This type of -nucleophile secures effective cleavage of water-stable substrates not only in alkaline but also in neutral and acidic media.