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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 42, 2012 - Issue 23
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Original Articles

Ph3P/I2-Catalyzed Beckmann Rearrangement of Ketoximes into Amides

Feng Xu Key Laboratory of Macromolecular Science of Shaanxi Province, School of Chemistry and Materials Science, Shaanxi Normal University, Xi'an, Shaanxi, ChinaCorrespondence[email protected]
,
Ni-Ge Wang Key Laboratory of Macromolecular Science of Shaanxi Province, School of Chemistry and Materials Science, Shaanxi Normal University, Xi'an, Shaanxi, China
,
You-Ping Tian Key Laboratory of Macromolecular Science of Shaanxi Province, School of Chemistry and Materials Science, Shaanxi Normal University, Xi'an, Shaanxi, China
,
Yong-Mei Chen Department of Chemistry, School of Science, Xi'an Jiaotong University, Xi'an, ChinaCorrespondence[email protected]
&
Wei-Chun Liu Key Laboratory of Macromolecular Science of Shaanxi Province, School of Chemistry and Materials Science, Shaanxi Normal University, Xi'an, Shaanxi, China
Pages 3532-3539 | Received 31 Mar 2011, Published online: 02 Aug 2012
 
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Abstract

A Beckmann rearrangement of ketoximes reaction using triphenylphosphine/iodine as an effective catalyst in acetonitrile at reflux temperature is reported. The results indicate that conversion of oximes to amides can be reached in good to excellent yields under optimal reaction conditions within several minutes. The reaction mechanism is also proposed. Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications to view the free supplemental file.

GRAPHICAL ABSTRACT

ACKNOWLEDGMENTS

This work was financially supported by the National Natural Science Foundation of China (20872085) and the Natural Science Foundation of Shaanxi Province (No. SJ08B22).

Notes

a Isolated yields.

a In CH3CN, reflux, 10 mol% Ph3P and 10 mol% I2 as catalyst.

b Isolated yields.

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