Reactions of 1,1-bis(silylmethyl)-1-alkene with N-halosuccinimide and ozone

被引：1

作者：

Uenishi, J ^{[1
]}

Tanaka, Y ^{[1
]}

Ohmi, M ^{[1
]}

Shimomura, H ^{[1
]}

Kawai, N ^{[1
]}

机构：

[1] Kyoto Pharmaceut Univ, Yamashina, Kyoto 6078412, Japan

来源：

HETEROCYCLES | 2005年 / 66卷

关键词：

allylsilane; protodesilylation; halodesilylation; oxidative desilylation; ozone;

D O I：

10.3987/COM-05-S(K)37

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Electrophilic reactions of 3-phenyl-1,1-bis(trimethylsilymethyl)-1-propene (1) and 1,1-bis[dimethyl(phenyl)silylmethyl]-3-phenyl-1-propene (4) are described. Protodesilylation of 1 with PPTS gave 2-substituted allylsilane (2) in excellent yield. Halogenation of 4 with N-halosuccimide gave a mixture of 3-halo-5-phenyl-2-silylmethyl-l-pentene (5) and 3-halo-5-phenyl-1,2bis(silylmethyl)-1-pentene (6). The reaction of 1 and 4 with ozone gave no carbonyl compounds but gave 3-hydoxy-5-phenyl-2-silylmethyl-1-pentene (7).

引用

页码：595 / 602

页数：8

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