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

被引：5
|
作者：
Yamazaki, S [1 ]
Yanase, Y
Yamamoto, K
机构：
[1] Nara Univ Educ, Dept Chem, Takabatake, Nara 6308528, Japan
[2] Osaka Univ, Grad Sch Sci, Dept Chem, Toyonaka, Osaka 5600043, Japan
来源：
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 2000年 / 12期
关键词：
D O I：
10.1039/a909919k
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The reactions of deuterio-labelled 1-seleno-2-silylethenes with trimethyl 2-phosphonoacrylate 2 and methyl vinyl ketone 4 in the presence of SnCl4 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 SnCl4 and ZnBr2 gave deuterium-substituted cyclobutanes without silicon migration. This labelling study strongly confirms the 1,2-silicon migration for [2+1] cycloadditions of 1 and non-1,2-silicon migration for the [2+2] cycloaddition reactions, respectively.
引用
收藏
页码：1991 / 1996
页数：6
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