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Paper | Regular issue | Vol 45, No. 3, 1997, pp.567-574
Published online, 1st January, 1970
DOI: 10.3987/COM-96-7718
Novel Preparation and Reaction of N-Benzenesulfonyl- and N-Methanesulfonyltroponimines. New Entry to 1-Azaazulene Derivatives

Tohru Takayasu, Hiroshi Katayama, and Makoto Nitta*

*Department of Chemistry, School of Science and Engineering, Waseda University, 3-4-1 Okubo, Shinjuku-ku, Tokyo 169-8555, Japan


N-Benzenesulfonyl- and N-methanesulfonyltroponimines were prepared through the reaction of tropone oxime with benzenesulfinyl- and methanesulfinyl chloride. The troponimines reacted with enamines to give formal [8+2] cycloadducts, which subsequently underwent elimination-dehydrogenation sequences to give 1-azaazulene derivatives in modest yields.