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Mechanistic insight into self-propagation in organo-mediated Beckmann rearrangement: A combined experimental and computational study.

Journal article
Authors N. An
B.-X. Tian
H.-J. Pi
Leif A Eriksson
W.-P. Deng
Published in Journal of Organic Chemistry
Volume 78
Issue 9
Pages 4297-4302
ISSN 0022-3263
Publication year 2013
Published at Department of Chemistry and Molecular Biology
Pages 4297-4302
Language en
Links dx.doi.org/10.1021/jo400278c
Subject categories Physical Chemistry, Organic Chemistry, Polymer Chemistry, Quantum chemistry

Abstract

Organo-mediated Beckmann rearrangement in the liquid phase, which has the advantage of high efficiency and straightforward experimental procedures, plays an important role in the synthesis of amides from oximes. However, the catalytic mechanisms of these organic-based promoters are still not well understood. In this work, we report a combined experimental and computational study on the mechanism of Beckmann rearrangement mediated by organic-based promoters, using TsCl as an example. A novel self-propagating cycle is proposed, and key intermediates of this self-propagating cycle are confirmed by both experiments and DFT calculations. In addition, the reason why cyclohexanone oxime is not a good substrate of the organo-mediated Beckmann rearrangement is discussed, and a strategy for improving the yield is proposed.

Page Manager: Webmaster|Last update: 9/11/2012
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