The mechanism of [2+ 1] and [2+ 2] cycloaddition reactions of 1-phenylseleno-2-(trimethylsilyl) ethene: an isotopic labelling study

S Yamazaki, Y Yanase, K Yamamoto

Index: Yamazaki, Shoko; Yanase, Yuichiro; Yamamoto, Kagetoshi Journal of the Chemical Society, Perkin Transactions 1, 2000 , # 12 p. 1991 - 1996

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Abstract

The reactions of deuterio-labelled 1-seleno-2-silylethenes with trimethyl 2- phosphonoacrylate 2 and methyl vinyl ketone 4 in the presence of SnCl 4 gave deuterio- substituted cyclopropanes with 1, 2-silicon migration. The reaction of deuterio-labelled 1- seleno-2-silylethenes with dimethyl 2, 2-dicyanoethene-1, 1-dicarboxylate 6 in the presence of SnCl 4 and ZnBr 2 gave deuterium-substituted cyclobutanes without silicon migration. ...