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An Efficient Synthesis of Dinitrile Derivatives by the Reaction of Oxime Esters or Acid Anhydrides with Cyanotrimethylsilane Catalyzed by La(OiPr)3

Akiko Fujii, Satoshi Sakaguchi and Yasutaka Ishii*

*Department of Applied Chemistry, Faculty of Engineering & High Technology, Research Center, Kansai University, Suita, Osaka 564-8680, Japan

A. Fujii, S. Sakaguchi, Y. Ishii, J. Org. Chem., 2000, 65, 6209-6212.

DOI: 10.1021/jo0055281

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La(OiPr)3 catalyzes a reaction of oxime esters or acid anhydrides with cyanotrimethylsilane (Me3SiCN) to provide α-trimethylsilyloxydinitrile derivatives in excellent yields. The reaction seems to proceed through the formation of acyl cyanides as intermediates.

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proposed mechanism

Key Words


ID: J42-Y2000