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Paper | Regular issue | Vol 29, No. 11, 1989, pp.2135-2140
Published online, 1st January, 1970
DOI: 10.3987/COM-89-5137
Thermal [4π+2π]-Type Cycloaddition Reactions of Pyrrole Derivatives with 3-Cyanocyclopropene Generated in situ

Katsuhiro Saito,* Kazuaki Ito, and Kensuke Takahashi

*Faculty of Engineering, Nagoya Institute of Technology, Gokiso-cho, Showa-ku, Nagoya 466-8555, Japan

Abstract

Thermal reactions of 3-cyanocyclopropene with 1-methoxycarbonyl-, 1-benzoyl-, and 1-phenylpyrroles afforded [4π+2π]-type cycloaddition products, while 1-methyl- and 1-methyl-3-acetylpyrroles did not give any adducts. The adduct of 1-benzoylpyrrole existed as a mixture of two rotamers because of the hindered rotation of the carbamate group.