Citation: 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 shu

Study of Oxidation of N-Sulfonylimines into Oxaziridines Catalyzed by Ammonium Halides

School of Pharmacy, Zunyi Medical University, Zunyi 563000

Corresponding author: Yao Qiuli, yaoqiuli@zmc.edu.cn
Received Date: 2 June 2016
Revised Date: 18 September 2016

Fund Project: the Science and Technology Foundation of Guizhou Province [2014]4002the Science and Technology Foundation of Guizhou Province [2014]7542the Zunyi Medical University F-627the National Natural Science Foundation of China 21462056the Education Department of Guizhou Province 201413653013

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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 tetramethylammonium 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.
- ammonium halides,
- N-sulfonyloxaziridines,
- oxaziridines,
- m-chloroperbenzoic acid
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