The Reaction of 4-Methylazoxybenzenes in Acidic Conditions under the Irradiation of UV-light
Jiro YAMAMOTO*, Hisato MIYAGAWA and Tomiya ISSHIKI
Department of Materials Science, Faculty of Engineering, Tottori University; Koyama-cho, Tottori-shi 680-8552 Japan
When the ethanol solutions of 4-methyl-NNO-azoxybenzene (1β) (α : β=0.0 : 1.0) and 4-methyl-ONN-azoxybenzene (1α) (α : β=3.0 : 1.0) were irradiated with UV light, respectively, α, β- and β, α-interconversion took place with the formation of 2-hydroxy-4'-methylazobenzene (2) as a rearrangement product. A lower yield of 2 and rapid α, β-isomerization from 1α to 1β were found in the UV iradiation of 1α (α : β=3.0 : 1.0) in sulfuric acid (60%--70% in concentration). Under the same reaction conditions,the less reactivities in ortho-migration from 1β to 2 and β, α-isomerization from 1β to 1α were observed in the irradiation of 1β (α : β=0.0 : 1.0).