Novel and Highly Selective Conversion of Alcohols and Thiols to Alkyl Nitrites with Triphenylphosphine/2,3-Dichloro-5,6-dicyanobenzoquinone/Bu4 NNO2 System

Batool Akhlaghinia; Ali Reza Pourali

doi:10.1055/s-2004-829122

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Synthesis 2004(11): 1747-1749
DOI: 10.1055/s-2004-829122

SHORTPAPER

Novel and Highly Selective Conversion of Alcohols and Thiols to Alkyl Nitrites with Triphenylphosphine/2,3-Dichloro-5,6-dicyanobenzoquinone/Bu₄ NNO₂System

Batool Akhlaghinia*, Ali Reza Pourali
Department of Chemistry, Damghan University of Basic Sciences, Damghan, Iran
Fax: +98(232)5244787; e-Mail: b_akhlaghinia@dubs.ac.ir;

Further Information

Publication History

Received 16 March 2004
Publication Date:
01 July 2004 (online)

Abstract
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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 is highly selective for the conversion of primary alcohols to alkyl nitrites in the presence of secondary and tertiary alcohols and thiols.

Key words

triphenylphosphine - 2,3-dichloro-5,6-dicyanobenzoquinone - alkyl nitrite - alcohol - thiol

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