4.3 Article

Ph3P/I2-CATALYZED BECKMANN REARRANGEMENT OF KETOXIMES INTO AMIDES

Journal

SYNTHETIC COMMUNICATIONS
Volume 42, Issue 23, Pages 3532-3539

Publisher

TAYLOR & FRANCIS INC
DOI: 10.1080/00397911.2011.585270

Keywords

Amide; Beckman rearrangement; iodine; ketoximes; triphenylphosphine

Funding

  1. National Natural Science Foundation of China [20872085]
  2. Natural Science Foundation of Shaanxi Province [SJ08B22]

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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.

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