Oxidation of N-naphthylhydroxylamines to nitrosonaphthols by air

Abstract

N-2-Naphthylhydroxylamine is oxidised by air in neutral or alkaline solution to 2-nitroso-1-naphthol, dibenzo[a,h]-phenazine, and 2,2′-azoxynaphthalene. N-1-Naphthylhydroxylamine is similarly oxidised to 4-nitroso-1-napthol. 2-Nitrosonaphthalene is oxidised to 2-nitroso-1-naphthol in the presence of an aerated solution of N-1-naphthylhydroxylamine or of N-biphenyl-4-ylhydroxylamine. N-2-Naphthylhydroxylamine reacts with thiols in neutral solution.