Reaction of triphenylphosphine with copper complexes derived from 2-nitrosophenols (1,2-quinone mono-oximes)

Abstract

Reaction of triphenylphosphine with the copper(II) complexes of 5-methoxy-2-nitrosophenol, 4-methyl-2-nitrosophenol, 1-nitroso-2-naphthol, and 2-nitroso-1-naphthol involves deoxygenation of one of the ligands to give 2-amino-7-methoxy-3H-phenoxazin-3-one, 4-methyl-2-aminophenol, 1-amino-2-naphthol, and 2-amino-N⁴-(1-hydroxy-2-naphthyl)-1,4-naphthoquinone 4-imine respectively as the major organic products. In all cases reduction of the metal occurs to give a complex of type Cu(qo)-(PPh₃)₂(qoH nitrosophenol). The reactions are rationalised in terms of nitrene intermediacy. An X-ray diffraction study of Cu(qo)(PPh₃)₂(qoH = 1-nitroso-2-naphthol) has been undertaken.