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Paper | Regular issue | Vol 34, No. 12, 1992, pp.2339-2348
Published online, 1st January, 1970
DOI: 10.3987/COM-92-6158
Formations of 1,1’-Biazaazulanones through [8+2]-Type Cycloaddition Reactions of Tropone Azine with Heterocumulenes

Kazuaki Ito, Katsuhiro Saito,* and Kensuke Takahashi

*Department of Applied Chemistry, Nagoya Institute of Technology, Gokiso-cho, Showa-ku, Nagoya 466, Japan

Abstract

Reaction of N-aryl-2,4,6-cycloheptatrien-1-imine with hydrazine afforded tropone azine, which reacted with chloroketenes to give 1,1’-biazaazulanones via [8+2]-type cycloadducts followed by elimination of hydrochloride. The similar reaction using phenyl isocyanate afforded a [8+2]-type 1:2 cycloadduct, while the reaction with phenyl isothiocyanate yielded only a 1:1 cycloadduct. 15N and 13C nmr spectra on C=N bond of tropne azine showed a minor contribution of a dipolar structure compared with the case of N-aryl-2,4,6-cycloheptatrien-1-imines.