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Paper | Regular issue | Vol 34, No. 3, 1992, pp.497-504
Published online, 1st January, 1970
DOI: 10.3987/COM-91-5916
Regioselective Cycloadditions of 1H-Azepine and 1H-1,2-Diazepine Derivatives with N,α-Diphenylnitrone and Nitrosobenzene

Katsuhiro Saito,* Akihiro Yoshino, Hiroyuki Watanabe, and Kensuke Takahashi

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

Abstract

Reactions of 1-carbomethoxy-1H-azepine with N,α-diphenylnitrone afforded endo- and exo-[2+3]-type cycloadducts in almost the same ratio. Reactions of 1-carboethoxy-1H-azepine with nitrosobenzene in chloroform afforded [4+2]- and [6+2]-types of cycloadducts. Analogous results were obtained in the reactions using 1-carboethoxy-1H-1,2-diazepine.