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Synthesis 2010(10): 1724-1730  
DOI: 10.1055/s-0029-1218711
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

An Efficient One-Pot Synthesis of Oxime Ethers from Alcohols Using Triphenylphosphine/Carbon Tetrachloride

Mohammad Navid Soltani Rad*a, Ali Khalafi-Nezhad*b, Fatemeh Karimitabarb, Somayeh Behrouza
a Department of Chemistry, Faculty of Basic Sciences, Shiraz University of Technology, Shiraz 71555-313, Iran
Fax: +98(711)7354523; e-Mail: soltani@sutech.ac.ir; e-Mail: nsoltanirad@gmail.com;
b Department of Chemistry, College of Sciences, Shiraz University, Shiraz 71454, Iran
Further Information

Publication History

Received 8 February 2010
Publication Date:
24 March 2010 (online)

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Abstract

A convenient and efficient one-pot O-alkylation of oximes from alcohols using triphenylphosphine in carbon tetrachloride is described. In this method, treatment of alcohols with a mixture of triphenylphosphine, carbon tetrachloride, oxime, and DBU in the presence of catalytic amounts of tetrabutylammonium iodide in refluxing acetonitrile regioselectively furnishes the corresponding O-alkyl ethers in good yields. This methodology is highly efficient O-alkylation of oximes with various structurally diverse alcohols. Semiempirical quantum-mechanic calculations (AM1) for unsymmetrical oxime ethers, indicated a lower heat of formation for Z-isomers.

Key words

oxime - alcohol - O-alkylation - triphenylphosphine - carbon tetrachloride - DBU

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