Oxidative nucleophilic substitution of hydrogen in nitroarenes with phenylacetonitrile derivatives

Article abstract of DOI:10.1016/S0040-4020(98)00472-4

Tertiary carbanions generated from α-substituted phenylacetonitriles in liquid ammonia add to nitrobenzenes 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.