A New and Convenient Method of Generating Alkyl Isocyanates from Alcohols­, Thiols and Trimethylsilyl Ethers Using Triphenylphosphine/2,3-Dichloro-5,6-dicyanobenzoquinone/Bu₄NOCN

Abstract

Alkyl isocyanates are prepared in good to excellent yields by treatment of alcohols, thiols and trimethylsilyl ethers with triphenylphosphine/2,3-dichloro-5,6-dicyanobenzoquinone/Bu₄NOCN in acetonitrile. This method is highly selective for conversion of primary alcohols to alkyl isocyanates in the presence of secondary and tertiary alcohols, thiols and trimethysilyl ethers.

triphenylphosphine - 2,3-dichloro-5,6-dicyanobenzoquinone - alcohol - thiol - trimethylsilyl ether - alkyl isocyanate

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