Oxidation of amines with peroxy radicals. I. N-phenyl-2-naphthylamine

Six products have been identified in the oxidation of N-phenyl-2-naphthylamine by peroxy radicals. Three of the products, 1,1 -bis(N-phenyl-2-naphthylamine) (2), N,N′-diphenyl-N-(2-naphthyl)-1,2-naphthylenediamine (3), and 7-phenyl-dibenzo[c,g]carbazole (4), are formed by the coupling of amino radicals. The remaining products, 2-anilino-1,4-naphthoquinone (5), 2-anilino-1,4-naphthoquinone-4-anil (6), and 4-(N-phenyl-2-naphthylamino)-1,2-naphthoquinone (7), are believed to be formed by the attack of various nucleophiles on 1,2-naphthoquinone-2-anil (10). This o-quinone imine was not identified among the products, but it is probably formed in the reaction of amino radicals with peroxy radicals.