The synthesis of azocine derivatives by the photocycloaddition of phenols to 1-naphthonitrile and 4-methoxy-1-naphthonitrile

Abstract

On irradiation of 1-naphthonitrile ( 1a) and 4-methoxy-1-naphthonitrile ( 1b) with a low pressure mercury arc lamp, photocycloaddition occurs to phenol ( 2a), 4-methylphenol ( 2b) and 4-methoxyphenol ( 2c) to give the substituted azocin-2(1H)-ones ( 4), formed from the initial 1,2-addition of the cyano group to the aromatic ring of the phenols.