SIMPLE PREPARATION OF TRIMETHYLSILYLACETONITRILE AND A NOVEL RING-OPENING OF EPOXIDES WITH TRIMETHYLSILYLACETONITRILE ANION

被引：86

作者：

MATSUDA, I

MURATA, S

ISHII, Y

机构：

[1] Department of Synthetic Chemistry, Faculty of Engineering, Nagoya University, Chikusa

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1979年 / 01期

关键词：

D O I：

10.1039/p19790000026

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Trimethylsilylacetonitrile (TMSAN) is prepared from halogenoacetonitrile and chlorotrimethylsilane using zinc as a halogen acceptor. TMSAN anion reacts with carbonyl compounds and epoxides to give αβ-unsaturated nitriles (1) and γ-trimethylsiloxynitriles (4) and (6), respectively. The formation of the latter compounds is explained by the intermediacy of (3) which is generated by 1,4-migration of the trimethylsilyl group. Nitriles (4) and (6) are readily transformed to γ-lactone derivatives (5) and (7) with hydrochloric acid in aqueous methanol.

引用

页码：26 / 30

页数：5

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