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Communication | Special issue | Vol 54, No. 2, 2001, pp.611-614
Published online, 1st January, 1970
DOI: 10.3987/COM-00-S(I)92
1,3-Dipolar Cycloaddition of 1-Phenylpropa-1,2-diene with Pyridinium Dicyanomethylides: 1-Phenylpropa-1,2-diene as a Synthetic Equivalent of 1-Phenylpropyne

Kiyoshi Matsumoto,* Naoki Tanaka, Takane Uchida, Yukio Ikemi, Naoto Hayashi, Kinuyo Aoyama, and Akikazu Kakehi

*Graduate School of Human and Environmental Studies, Kyoto University, Kyoto 606-8501, Japan

Abstract

Pyridinium dicyanomethylides (1) underwent 1, 3-dipolar cycloaddition with 1-phenyl-propa-1,2-diene (2) to give a mixture of 3-cyano-2-methyl-1-phenylindolizines (4) and 3-cyano-1-methyl-2-phenylindolizines (5), accompanied by dehydrocyanation and 1, 3-sigmatropic hydrogen shift.