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Communication | Regular issue | Vol 22, No. 3, 1984, pp.457-460
Published online, 1st January, 1970
DOI: 10.3987/R-1984-03-0457
Re-exploratiom of the Thermolysis of Arylazides as a Route to 3H-Azepines: Chemistry of Azidoacetophenones

Yoshihiro Ohba,* Shinji Kubo, Tarozaemon Nishiwaki, and Noritoshi Aratani

*Department of Chemistry, Faculty of Science, Yamaguchi University, 1677-1 Yoshida, Yamaguchi 753-8512, Japan

Abstract

Thermolysis of 3-azidoacetophenone in methanol in a sealed glass ampoule gave 6-acetyl- and 4-acetyl-3H-azepines in moderate yields, whose kinetic data [Ea=132.6 ± 1.7 kJmol-1, ΔS443= -12.1 ± 4.2 JK-1 mol-1] were obtained by means of HPLC. Photolysis of this azide in methanol gave the same pair of the 3H-azepines in poor yields. Thermolysis of 4-azidoacetophenone under the similar conditions afforded a moderate yield of 5-acetyl-3H-azepine. For comparison, photolyses of 4- and 2-azidoacetophenones were also studied.