Oxidative nucleophilic substitution of hydrogen in nitroarenes with phenylacetonitrile derivatives

Abstract

Tertiary carbanions generated from α-substituted phenylacetonitriles in liquid ammonia add to nitro-benzenes in the para position to form the corresponding σ H-adducts which are transformed, depending on the starting nitriles and the reaction conditions, to products of oxidative nucleophilic substitution of hydrogen, ONSH or vicarious nucleophilic substitution, VNS.