Novel and Highly Selective Conversion of Alcohols and Thiols to Alkyl Nitrites with Triphenylphosphine/2,3-Dichloro-5,6-dicyanobenzoquinone/Bu₄NNO₂ System

Batool Akhlaghinia*, Ali Reza Pourali

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

B. Akhlaghinia, A. R. Pourali, Synthesis, 2004, 1747-1749.

DOI: 10.1055/s-2004-829122

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Abstract

Alkyl nitrites were prepared in good to excellent yields by treatment of alcohols and thiols with triphenylphosphine/2,3-dichloro-5,6-dicyanobenzoquinone/Bu₄NNO₂ in acetonitrile. This method allows a highly selective conversion of primary alcohols in the presence of secondary and tertiary alcohols and thiols.

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Key Words

triphenylphosphine, 2,3-dichloro-5,6-dicyanobenzoquinone, alkyl nitrites, alcohols, thiols

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ID: J66-Y2004-2190