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Synthesis 2010(21): 3705-3709  
DOI: 10.1055/s-0030-1258217
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© Georg Thieme Verlag Stuttgart ˙ New York

Efficient Iodine-Mediated Beckmann Rearrangement of Ketoximes to Amides under Mild Neutral Conditions

Nemai C. Ganguly*, Pallab Mondal
Department of Chemistry, University of Kalyani, Kalyani 741235, WB, India
Fax: +91(33)25828282 ; e-Mail: nemai_g@yahoo.co.in;
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Publication History

Received 24 June 2010
Publication Date:
18 August 2010 (online)

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Abstract

Aryl ketoximes readily underwent Beckmann rearrangement to give N-substituted amides in excellent yields on electrophilic activation by elemental iodine in anhydrous acetonitrile under reflux. The main advantages of this environmentally friendly protocol include a high selectivity as a result of the absence of any accompanying deprotection to form the parent ketones as byproducts, mild neutral conditions, procedural simplicity, and particularly ease of isolation of the products.

Key words

rearrangements - amides - ketoximes - catalysis - Beckmann rearrangements