An efficient synthesis of dinitrile derivatives by the reaction of oxime esters or acid anhydrides with cyanotrimethylsilane catalyzed by La(O(i)Pr)3

被引：16

作者：

Fujii, A ^{[1
]}

Sakaguchi, S ^{[1
]}

Ishii, Y ^{[1
]}

机构：

[1] Kansai Univ, Fac Engn & High Technol, Res Ctr, Dept Appl Chem, Suita, Osaka 5648680, Japan

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2000年 / 65卷 / 19期

关键词：

D O I：

10.1021/jo0055281

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The reaction of oxime esters with cyanotrimethylsilane (Me3SiCN) under the influence of a catalytic amount of lanthanide compounds produced alpha-trimethylsilyloxydinitrile derivatives in excellent yields accompanied with the formation of trimethylsilyl oxime ethers. Among the lanthanoid catalysts examined, La((OPr)-Pr-i)(3) was found to be the best catalyst. The reaction seems to proceed through the formation- of acyl cyanides as intermediates, followed by the addition of Me3SiCN to them. Additionally, the reaction of acetic anhydride with Me3SiCN catalyzed by La((OPr)-Pr-i)(3) gave 1-trimethylsilyloxyethane dinitrile. Thus, various alpha-trimethylsilyloxydinitriles were synthesized in good yields by allowing oxime esters or acid anhydrides to react with Me3SiCN in the presence of a catalytic amount of La((OPr)-Pr-i)(3).

引用

页码：6209 / 6212

页数：4

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