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Communication | Special issue | Vol 52, No. 2, 2000, pp.541-544
Published online, 1st January, 1970
DOI: 10.3987/COM-99-S66
Novel Synthesis of Oxadiazinone and Oxadiazepinone Derivatives by Ring Expansion of Diaziridinone

Mitsuo Komatsu,* Norio Sakai, Akira Hakotani, Satoshi Minakata, and Yoshiki Ohshiro

*Faculty of Engineering, Department of Applied Chemistry, Osaka University, 2-1 Yamadaoka, Toyonaka, Osaka 560-0043, Japan

Abstract

Treatment of N, N'-di-tert-butyldiaziridinone with α-hydroxy ketones in the presence of a catalytic amount of BF3·OEt2 gave carbazate derivatives in excellent yields. Acid-catalyzed recyclization of these compounds easily proceeded to give oxadiazinone derivatives. The reaction was applicable to the synthesis of oxadiazepinone derivatives and also to one-pot process.