The Oxygen Transfer Reaction of 4-Acetylazoxybenzenes in Sulfuric Acid
Jiro YAMAMOTO*, Kenji HAMANAKA and Takasi TSUBOI
Department of Materials Science, Faculty of Engineering, Tottori University; Koyama-cho, Tottori-shi 680-8552 Japan
When the starting materials 4-acetyl-ONN- and -NNO-azoxybenzene(1α and 1β, respectively) were heated in 70/80% sulfuric acid, α/β isomerization and the Wallach rearrangement to 4-acetyl-4'-hydroxyazobenzene (2) were observed. However, neither the o-hydroxyazobenzene nor 4-acetyl azobenzene was detected in the reaction product. The isomerization of 1α was faster than that of 1β, demonstrating the higher themodynamic stability of the latter.
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