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Communication | Regular issue | Vol 55, No. 3, 2001, pp.465-468
Published online, 1st January, 1970
DOI: 10.3987/COM-00-9152
Novel Ring Transformation of Dihydroselenines to Selenabicyclo[3.1.0]hexenes

Eiji Honda, Shin-ichi Watanabe, Tatsunori Iwamura, and Tadashi Kataoka*

*Gifu Pharmaceutical University, 6-1 Mitahora-higashi 5-chome, Gifu 502-8585, Japan

Abstract

Treatment of 2-bromo-2,6-dicyano-2,3-dihydroselenine (6) with triethylamine in ethanol gave 2-selenabicyclo[3.1.0]hex-3-ene (7) in 77% yield. Reaction of 7 with benzyne formed benzoselenophene (11) in 35% yield. Methylation of 7 with methyl triflate produced Se-methylselenonium salt (12), which was transformed into amide derivatives (16) and (17). Compound (7) was converted into alkynylcyclopropane (13) via selenonium salt (12).