Photochemical reactions of azo compounds. XVII Photoinduced reaction of 2,2,4,4,-tetrachloroazobenzene with acetyl chloride

Abstract

The photoinduced reaction of 2,2',4,4'-tetrachloroazobenzene with acetyl chloride has been found to give an unexpected mixture of products, incorporating only a relatively poor yield of the predicted main product, N,N '-diacetyl-2,2',4,4',6-pentachlorohydrazobenzene. It has been found, moreover, that the latter compound in aqueous methanolic potassium hydroxide, in addition to yielding the expected hydrolysis/oxidation product, 2,2',4,4',6-pentachloroazobenzene, undergoes an interesting side reaction which regenerates 2,2',4,4'-tetrachloroazobenzene.