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

Batool Akhlaghinia*

*Department of Chemistry, Damghan University of Basic Sciences, Damghan, Iran, Email: b_akhlaghiniadubs.ac.ir

B. Akhlaghinia, Synthesis, 2005, 1955-1958.

DOI: 10.1055/s-2005-869906

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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.

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Key Words

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

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ID: J66-Y2005-1210