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Communication | Regular issue | Vol 36, No. 1, 1993, pp.21-24
Published online, 1st January, 1970
DOI: 10.3987/COM-92-6182
1,3-Dipolar Cycloaddition Reactions of N-Aryl-2,4,6-cycloheptarien-1-imines with p-Substituted Benzonitrile Oxides: Formations of 1,2,4-Oxadiazaspiro[4.6]undeca-6,8,10-trienes

Kazuaki Ito, Katsuhiro Saito,* and Kensuke Takahashi

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

Abstract

Reactions of N-aryl-2,4,6-cycloheptatrien-1-imines with p-substituted benzonitrile oxides afforded 1,2,4-oxadiazaspiro[4.6]undeca-6,8,10-trienes via [2+4] type cycloadditions. The study of substituent effects on the reaction rates suggested the nucleophilic attacks of the imines to the nitrile oxides.