Synlett 2005(9): 1456-1458  
DOI: 10.1055/s-2005-868511
LETTER
© Georg Thieme Verlag Stuttgart · New York

Direct Oxidative Conversion of Primary Alcohols to Nitriles Using Molecular Iodine in Ammonia Water

Naoshi Moria, Hideo Togo*a,b
a Graduate School of Science and Technology, Chiba University, Yayoi-cho 1-33. Inage-ku, Chiba 263-8522, Japan
b Department of Chemistry, Faculty of Science, Chiba University, Yayoi-cho 1-33. Inage-ku, Chiba 263-8522, Japan
Fax: +81(43)2902874; e-Mail: togo@faculty.chiba-u.jp;
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Publikationsverlauf

Received 23 March 2005
Publikationsdatum:
29. April 2005 (online)

Abstract

A simple, effective, high-yield procedure for the direct oxidative conversion of alcohols to nitriles, was successfully carried out with molecular iodine in ammonia water.

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CAUTION: It is known that iodine reacts with ammonia water under certain conditions to give a black powder of nitrogen triiodide monoamine (NI3·NH3). The dry powder explodes readily by mechanical shock, heat or irradiation. Although we did not have any incidents in this study, one should be careful.

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Online data from Sigma-Aldrich products;
http://www.sigmaaldrich.com/Brands/Aldrich.html