Chinese Journal of Organic Chemistry >
Study of Oxidation of N-Sulfonylimines into Oxaziridines Catalyzed by Ammonium Halides
Received date: 2016-06-02
Revised date: 2016-09-08
Online published: 2016-09-12
Supported by
Project supported by the National Natural Science Foundation of China(No. 21462056), the Science and Technology Foundation of Guizhou Province(Nos.[2014]7542,[2014]4002), the Education Department of Guizhou Province(No. 201413653013), and the Zunyi Medical University(No. F-627).
The method of oxidation of N-sulfonylimines to N-sulfonyloxaziridines with m-chloroperbenzoic acid catalyzed by ammonium halides was systematically investigated for the first time.Tetraethylammonium halides(Et4NI or Et4NCl) and tet-ramethylammonium halides(Me4NI,Me4NBr or Me4NCl) were firstly used to catalyze the oxidation of a series of N-sulfonylimines to the corresponding N-sulfonyloxaziridines in excellent yields.The experimental results showed that the alkyl group of the ammonium had significant influence on the reaction,whereas the halide ions had lesser influence on the reaction.Thus the research has provided a simple procedure for the preparation of oxaziradine with excellent yields.
Yao Qiuli , Huang Xiaoli , Pu Jiazhi , Xi Xianxiu , Fang Xuehong , Zhao Ling , Mai Youqun , He Chunyang . Study of Oxidation of N-Sulfonylimines into Oxaziridines Catalyzed by Ammonium Halides[J]. Chinese Journal of Organic Chemistry, 2017 , 37(1) : 116 -121 . DOI: 10.6023/cjoc201606005
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