Photochemical reactions of azo compounds. VIII. Photochemical rearrangement of 2,2'-dimethylazoxybenzene

Abstract

It has been found that the photochemical rearrangement of 2,2?- dimethyl-azoxybenzene to 2-hydroxy-6,2?-dimethylazobenzene (major product) is accompanied by the formation of 4-hydroxy-2,2?- dimethylazobenzene and 2-hydroxy-4,2?-dimethylazobenzene in small yields. α-2,4,6-Trimethylazoxybenzene was shown not to isomerize when irradiated. It is concluded that the minor photochemical products from 2,2?-dimethylazoxybenzene do not arise as a result of migration of ring substituents. A reaction mechanism, which would account for the minor products, is tentatively suggested.