Synthesis 2012; 44(18): 2903-2909
DOI: 10.1055/s-0032-1316747
paper
© Georg Thieme Verlag Stuttgart · New York

A Simple and Effective Synthesis of Benzolactones and Benzolactams by Noncatalytic­ Benzylic Oxidation of Cyclic Benzylic Ethers and N-Protected Cyclic Benzylic Amines with Sodium Chlorite as an Oxidant

Ai-Ru Song
a   State Key Laboratory of Elemento-Organic Chemistry, The Research Institute of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, P. R. of China, Fax: 86(22)23503627   Email: zhangchi@nankai.edu.cn
b   Tianjin Key Laboratory of Water Resources and Environment, Tianjin Normal University, Tianjin 300387, P. R. of China
,
Jun Yu
a   State Key Laboratory of Elemento-Organic Chemistry, The Research Institute of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, P. R. of China, Fax: 86(22)23503627   Email: zhangchi@nankai.edu.cn
,
Chi Zhang*
a   State Key Laboratory of Elemento-Organic Chemistry, The Research Institute of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, P. R. of China, Fax: 86(22)23503627   Email: zhangchi@nankai.edu.cn
› Author Affiliations
Further Information

Publication History

Received: 04 May 2012

Accepted after revision: 20 June 2012

Publication Date:
30 July 2012 (online)


Abstract

Sodium chlorite (NaClO2) was shown to be capable of oxidizing cyclic benzylic ethers and N-protected cyclic benzylic amines in a heterogeneous solvent system of 1,1,1-trichloroethane and water at 55–65 °C to give synthetically useful benzolactones and benzolactams, respectively, in high-to-excellent yields.

Supporting Information

 
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