Reactivity of primary and secondary amines with 2-nitrophenazine 10-oxide

Abstract

The nucleophilic substitution of primary and seondary amines on 2-nitrophenazine 10-oxide (1) was examined for homogeneous media. The formation, under the reaction conditions, of a σ anionic Meisenheimer complex was demonstrated by absorbance, conductance, and n.m.r. measurements. The photochemical reaction in the presence of primary and secondary amines caused mainly two reactions, the reduction of (1) to 2-nitrophenazine and the substitution of the nitro-group by the amino-group.