The Photochemical Reduction of Hydrazobenzene

Abstract Hydrazobenzene was irradiated with an ultraviolet light in n-hexane under a nitrogen atmosphere. The products were azobenzene, aniline, and a trace of semidines. The yield of azobenzene was usually larger than that calculated on the basis of the disproportionation of hydrazobenzene, while the yield of aniline was less. The reactions were followed by the determination of the disappearance of hydrazobenzene and that of the formation of azobenzene. On the basis of the available data, in the photochemical reaction of hydrazobenzene it was assumed that the formation of azobenzene was not due to the disproportionation, but to the oxidation of hydrazobenzene, and that no fission of the N–N bond of hydrazobenzene occurred to give azobenzene.