Photochemical reactions of primary amines on nitrophenazines

Abstract

The photochemical nucleophilic substitution reactions of some primary amines on 2-nitrophenazine produce good yields of 6- and 9-alkylamino-2-nitrophenazines with minor amounts of 4-alkylamino-2-nitrophenazine. Irradiation of 1-nitrophenazine yields 6- and 9-alkylamino-1-nitrophenazines in addition to other products which are formed thermally. The regioselectivity of this reaction is discussed and compared with the orientation rules of Havinga and Cornelisse. An addition–elimination mechanism is proposed.