Photochemical reactions of azo compounds. XV. Ortho/para substitution ratios in the photoinduced reactions of trans-azobenzene with acid chlorides

Abstract

Irradiation of trans-azobenzene in acetyl chloride, and subsequent hydrolysis-oxidation of the photo product, has been shown to yield a small amount of 2-chloroazo-benzene in addition to 4-chloroazobenzene (main product). Analogous reaction sequences, starting with different acid chlorides, show marked variations in ortho/para substitution ratios; and correlations indicate that the relative extents of ortho and para substitution are associated with the ionizability of the acid chlorides.