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
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
收藏
页码:6209 / 6212
页数:4
相关论文
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