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Communication | Regular issue | Vol 57, No. 2, 2002, pp.235-240
Published online, 1st January, 1970
DOI: 10.3987/COM-01-9416
■ [2π+2σ] Type Cycloaddition Reactions of Iminotropone Derivatives with Naphtho[b]cyclopropene to Form Cyclic Amine Compounds

Katsuhiro Saito,* Katsuhiko Ono, Narie Ito, Naoe Tada, and Shinichi Ando

*Department of Applied Chemistry, Nagoya Institute of Technology, Gokiso-cho, Showa-ku, Nagoya 466-8555, Japan

Abstract

Reactions of iminotropone derivatives with naphtho[b]cyclopropene under the presence of a catalytic amount of AgBF4 afforded cyclic amine derivatives via [2π+ 2σ] type cycloaddition reactions. On the other hand, a reaction using a tropone hydrazone derivative without a catalysis formed a substituted hydrazone via a σ-bond rupture of the cyclopropene ring.