Issue 30, 2016

Transition-metal-free oxychlorination of alkenyl oximes: in situ generated radicals with tert-butyl nitrite

Abstract

Oxychlorination of alkenyl oximes is harder compared to the analogous oxybromination or oxyiodination because of the difficulty associated with the formation of chlorine cations or radicals. A transition-metal-free oxychlorination of alkenyl oximes has been developed, using t-BuONO as a dual oxidant and AlCl3 as a chlorine source. This convenient and practical method has been used to construct chloroisoxazolines in moderate to good yields, whereas N-chlorosuccinimide (NCS) failed to promote this reaction.

Graphical abstract: Transition-metal-free oxychlorination of alkenyl oximes: in situ generated radicals with tert-butyl nitrite

Supplementary files

Article information

Article type
Paper
Submitted
25 Jun 2016
Accepted
05 Jul 2016
First published
05 Jul 2016

Org. Biomol. Chem., 2016,14, 7275-7281

Transition-metal-free oxychlorination of alkenyl oximes: in situ generated radicals with tert-butyl nitrite

X. Zhang, Z. Xiao, M. Wang, Y. Zhuang and Y. Kang, Org. Biomol. Chem., 2016, 14, 7275 DOI: 10.1039/C6OB01374K

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