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

Figures(2)

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
1. [1]
  Williamson, K. S.; Michaelis, D. J.; Yoon. T. P. Chem. Rev. 2014, 114, 8016. doi: 10.1021/cr400611n
2. [2]
  Della, S. G.; Lattanzi, A. ACS Catal. 2014, 4, 1234. doi: 10.1021/cs500132m
3. [3]
  Mlochowski, J.; Kubicz, E.; Kloc, K.; Mordarski, M.; Peczynska, W.; Syper, L. Liebigs Ann. Chem. 1988, 455.
4. [4]
  Benkovics, T.; Guzei, I. A.; Yoon T. P. Angew. Chem., Int. Ed. 2010, 49, 9153. doi: 10.1002/anie.201004635
5. [5]
  Williamson, K. S.; Yoon T. P. J. Am. Chem. Soc. 2010, 132, 4570. doi: 10.1021/ja1013536
6. [6]
  Spencer, W. T. III; Levin, M. D.; Frontier, A. J. Org. Lett. 2011, 13, 414. doi: 10.1021/ol1027255
7. [7]
  Schoumacker, S.; Hamelin, O.; Téti, S.; Pécaut, J.; Fontecave, M. J. Org. Chem. 2005, 301.
8. [8]
  Armstrong, A.; Challinor, L.; Moir, J. H. Angew. Chem., Int. Ed. 2007, 46, 5369. doi: 10.1002/(ISSN)1521-3773
9. [9]
  Paleo, M. R.; Aurrecoechea, N.; Jung, K.-Y.; Rapoport, H. J. Org. Chem. 2003, 68, 130. doi: 10.1021/jo0206521
10. [10]
  Han, S.; Movassaghi, M. J. Am. Chem. Soc. 2011, 133, 10768. doi: 10.1021/ja204597k
11. [11]
  Zou, L.; Wang, B.; Mu, H.; Zhang, H.; Song, Y.; Qu, J. Org. Lett. 2013, 15, 3106. doi: 10.1021/ol401306h
12. [12]
  Smith, S. R.; Fallan, C.; Taylor, J. E.; McLennan, R.; Daniels, D. S. B.; Morrill, L. C.; Slawin, A. M. Z.; Smith, A. D. Chem. Eur. J. 2015, 21, 10530. doi: 10.1002/chem.201501271
13. [13]
  Panlin, S.; Litao, S.; Song, Y. Chin. J. Chem. 2012, 30, 2688.
14. [14]
  Kondoha, A.; Terada, M. Org. Chem. Front. 2015, 2, 801. doi: 10.1039/C5QO00108K
15. [15]
  Peng, X.; Zhu, Y.; Ramirez, T. A.; Zhao, B.; Shi, Y. Org. Lett. 2011, 13, 5244. doi: 10.1021/ol2021252
16. [16]
  Allen, C. P.; Benkovics, T.; Turek, A. K.; Yoon, T. P. J. Am. Chem. Soc. 2009, 131, 12560. doi: 10.1021/ja906183g
17. [17]
  Foot, O. F.; Knight, D. W. Chem. Commun. 2000, 975.
18. [18]
  Vishwakarma, L. C.; Stringer, O. D.; Davis, F. A. Org. Synth. 1988, 66, 203. doi: 10.15227/orgsyn.066.0203
19. [19]
  Towson, J. C.; Weismiller, M. C.; Lal, G. S.; Sheppard, A. C.; Kumar, A.; Davis, F. A. Org. Synth. 1990, 69, 158. doi: 10.15227/orgsyn.069.0158
20. [20]
  Davis, F. A.; Nadir, U. K.; Kluger, E. W. J. Chem. Soc., Chem. Commun. 1977, 25.
21. [21]
  Ruano, J. L. G.; Aleman, J.; Fajardo, C.; Parra, A. Org. Lett. 2005, 7(24), 5493.
22. [22]
  Chang, J. W. W.; Ton, T. M. U.; Tania, S.; Taylor, P. C.; Chan, P. W. H. Chem. Commun. (Cambridge, U. K.) 2010, 46(6), 922. doi: 10.1039/B918588G
23. [23]
  Davis, F. A.; Stringer, O. D. J. Org. Chem. 1982, 47, 1774. doi: 10.1021/jo00348a039
24. [24]
  Davis, F. A.; Chattopadhyay, S.; Towson, J. C.; Lal, S.; Reddy, T. J. Org. Chem. 1988, 53, 2087. doi: 10.1021/jo00244a043
25. [25]
  Murphy, J. A.; Mahesh, M.; McPheators, G.; Anand, R. V.; McGuire, T. M.; Carling, R.; Kennedy, A. R. Org. Lett. 2007, 9, 3233. doi: 10.1021/ol071049d
26. [26]
  El-Dakdouki, M. H.; Adamski, N.; Foster, L.; Hacker, M. P.; Erhardt, P. W. J. Med. Chem. 2011, 54, 8224. doi: 10.1021/jm200984x
27. [27]
  Peng, L.; Chen, C.; Gonzalez, C. R.; Balogh-Nair, V. Int. J. Mol. Sci. 2002, 3, 1145. doi: 10.3390/i3111145
28. [28]
  Kui, L.; Ohyun, K. Org. Synth. 2009, 86, 212. doi: 10.15227/orgsyn.086.0212
29. [29]
  Davis, F. A.; Lamendola, J. Jr.; Nadir, U.; Kluger, E. W.; Sedergran, T. C.; Panunto, T. W.; Billmers, R.; Jenkins, R., Jr.; Turci, I. J.; Watson, W. H.; Chen, J. S.; Kimura, M. J. Am. Chem. Soc. 1980, 102, 2000. doi: 10.1021/ja00526a040
30. [30]
  Chen, D.; Chen, X.; Du, T.; Kong, L.; Zhen, R.; Zhen, S.; Wen, Y.; Zhu, G. Tetrahedron Lett. 2010, 51(39), 5131. doi: 10.1016/j.tetlet.2010.07.087
31. [31]
  Syu, S.; Lee, Y.; Jang, Y.; Lin, W. J. Org. Chem. 2011, 76(8), 2888. doi: 10.1021/jo102143r
32. [32]
  Jin, T.; Yu, M.; Liu, L.; Zhao, Y.; Li, T. Synth. Commun. 2006, 36(16), 2339. doi: 10.1080/00397910600640073
33. [33]
  Jin, T.; Feng, G.; Yang, M.; Li, T. Synth. Commun. 2004, 34(7), 1277. doi: 10.1081/SCC-120030315
34. [34]
  Jin, T.; Feng, G.; Yang, M.; Li, T. J. Chem. Res., Synop. 2003, (9), 591.
35. [35]
  Barbarotto, M.; Geist, J.; Choppin, S.; Colobert, F. Tetrahedron: Asymmetry 2009, 20(24), 2780. doi: 10.1016/j.tetasy.2009.11.020
36. [36]
  Jain, S. L.; Sharma, V. B.; Sain, B. J. Mol. Catal. A: Chem. 2005, 239(1-2), 92.
37. [37]
  Ton, T. M. U. C.; Tania, T. S.; Chang, J. W. W.; Chan, P. W. H. J. Org. Chem. 2011, 76(12), 4894. doi: 10.1021/jo200284a
38. [38]
  Williams, D. R.; Robinson, L. A.; Bawel, S. A. Tetrahedron Lett. 2015, 56(23), 3200. doi: 10.1016/j.tetlet.2014.12.049
39. [39]
  Lykke, L.; Rodriguez-Escrich, C.; Jorgensen, K. A. J. Am. Chem. Soc. 2011, 133(38), 14932. doi: 10.1021/ja2064457
40. [40]
  Klein, M.; Ugi, I. Z. Naturforsch., B: J. Chem. Sci. 1992, 47(6), 887.
41. [41]
  Dong, S.; Liu, X.; Zhu, Y.; He, P.; Lin, L.; Feng, X. J. Am. Chem. Soc. 2013, 135(27), 10026. doi: 10.1021/ja404379n
42. [42]
  Zhang, T.; He, W.; Zhao, X.; Jin, Y. Tetrahedron 2013, 69, 7416. doi: 10.1016/j.tet.2013.06.061
1. [1]
  Jiatong Hu , Qiyi Wang , Ruiwen Tang , Jiajing Feng . Photocatalytic Journey of Perylene Diimides in a Competitive Arena. University Chemistry, 2025, 40(5): 328-333. doi: 10.12461/PKU.DXHX202407015
2. [2]
  Caixia Lin , Ting Liu , Zhaojiang Shi , Hong Yan , Keyin Ye , Yaofeng Yuan . Innovative Experiment of Electrochemical Dearomative Spirocyclization of N-Acyl Sulfonamides. University Chemistry, 2025, 40(4): 359-366. doi: 10.12461/PKU.DXHX202406107
3. [3]
  Jiaxin Su , Jiaqi Zhang , Shuming Chai , Yankun Wang , Sibo Wang , Yuanxing Fang . Optimizing Poly(heptazine imide) Photoanodes Using Binary Molten Salt Synthesis for Water Oxidation Reaction. Acta Physico-Chimica Sinica, 2024, 40(12): 2408012-. doi: 10.3866/PKU.WHXB202408012
4. [4]
  Jizhou Liu , Chenbin Ai , Chenrui Hu , Bei Cheng , Jianjun Zhang . 六氯锡酸铵促进钙钛矿太阳能电池界面电子转移及其飞秒瞬态吸收光谱研究. Acta Physico-Chimica Sinica, 2024, 40(11): 2402006-. doi: 10.3866/PKU.WHXB202402006
5. [5]
  Jingjie Tang , Luying Xie , Jiayu Liu , Shangyu Shi , Xinyu Sun , Jiayang Lin , Qikun Yang , Chuan'ang Yu , Zecheng Wang , Yingying Wang , Zengyang Xie . Efficient Rapid Synthesis and Antibacterial Activities of Tosylhydrazones: A Recommended Innovative Chemistry Experiment for Undergraduate Medical University. University Chemistry, 2024, 39(3): 316-326. doi: 10.3866/PKU.DXHX202309091
6. [6]
  Lirui Shen , Kun Liu , Ying Yang , Dongwan Li , Wengui Chang . Synthesis and Application of Decanedioic Acid-N-Hydroxysuccinimide Ester: Exploration of Teaching Reform in Comprehensive Applied Chemistry Experiment. University Chemistry, 2024, 39(8): 212-220. doi: 10.3866/PKU.DXHX202312035
7. [7]
  Ling Liu , Haibin Wang , Genrong Qiang . Curriculum Ideological and Political Design for the Comprehensive Preparation Experiment of Ethyl Benzoate Synthesized from Benzyl Alcohol. University Chemistry, 2024, 39(2): 94-98. doi: 10.3866/PKU.DXHX202304080
8. [8]
  Yikai Wang , Xiaolin Jiang , Haoming Song , Nan Wei , Yifan Wang , Xinjun Xu , Cuihong Li , Hao Lu , Yahui Liu , Zhishan Bo . 氰基修饰的苝二酰亚胺衍生物作为膜厚不敏感型阴极界面材料用于高效有机太阳能电池. Acta Physico-Chimica Sinica, 2025, 41(3): 2406007-. doi: 10.3866/PKU.WHXB202406007
9. [9]
  Yi DING , Peiyu LIAO , Jianhua JIA , Mingliang TONG . Structure and photoluminescence modulation of silver(Ⅰ)-tetra(pyridin-4-yl)ethene metal-organic frameworks by substituted benzoates. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 141-148. doi: 10.11862/CJIC.20240393
10. [10]
  Rui Li , Huan Liu , Yinan Jiao , Shengjian Qin , Jie Meng , Jiayu Song , Rongrong Yan , Hang Su , Hengbin Chen , Zixuan Shang , Jinjin Zhao . 卤化物钙钛矿的单双向离子迁移. Acta Physico-Chimica Sinica, 2024, 40(11): 2311011-. doi: 10.3866/PKU.WHXB202311011
11. [11]
  Yahui HAN , Jinjin ZHAO , Ning REN , Jianjun ZHANG . Synthesis, crystal structure, thermal decomposition mechanism, and fluorescence properties of benzoic acid and 4-hydroxy-2, 2′: 6′, 2″-terpyridine lanthanide complexes. Chinese Journal of Inorganic Chemistry, 2025, 41(5): 969-982. doi: 10.11862/CJIC.20240395
12. [12]
  Xinhao Yan , Guoliang Hu , Ruixi Chen , Hongyu Liu , Qizhi Yao , Jiao Li , Lingling Li . Polyethylene Glycol-Ammonium Sulfate-Nitroso R Salt System for the Separation of Cobalt (II). University Chemistry, 2024, 39(6): 287-294. doi: 10.3866/PKU.DXHX202310073
13. [13]
  Jihua Deng , Xinshi Wu , Dichang Zhong . Exploration of Green Teaching and Ideological and Political Education in Chemical Experiment of “Preparation of Ammonium Ferrous Sulfate”. University Chemistry, 2024, 39(10): 325-329. doi: 10.12461/PKU.DXHX202405046
14. [14]
  Pengcheng Yan , Peng Wang , Jing Huang , Zhao Mo , Li Xu , Yun Chen , Yu Zhang , Zhichong Qi , Hui Xu , Henan Li . Engineering Multiple Optimization Strategy on Bismuth Oxyhalide Photoactive Materials for Efficient Photoelectrochemical Applications. Acta Physico-Chimica Sinica, 2025, 41(2): 100014-. doi: 10.3866/PKU.WHXB202309047
15. [15]
  Kaihui Huang , Dejun Chen , Xin Zhang , Rongchen Shen , Peng Zhang , Difa Xu , Xin Li . Constructing Covalent Triazine Frameworks/N-Doped Carbon-Coated Cu₂O S-Scheme Heterojunctions for Boosting Photocatalytic Hydrogen Production. Acta Physico-Chimica Sinica, 2024, 40(12): 2407020-. doi: 10.3866/PKU.WHXB202407020
16. [16]
  Caixia Lin , Zhaojiang Shi , Yi Yu , Jianfeng Yan , Keyin Ye , Yaofeng Yuan . Ideological and Political Design for the Electrochemical Synthesis of Benzoxathiazine Dioxide Experiment. University Chemistry, 2024, 39(2): 61-66. doi: 10.3866/PKU.DXHX202309005
17. [17]
  Renqing Lü , Shutao Wang , Fang Wang , Guoping Shen . Computational Chemistry Aided Organic Chemistry Teaching: A Case of Comparison of Basicity and Stability of Diazine Isomers. University Chemistry, 2025, 40(3): 76-82. doi: 10.12461/PKU.DXHX202404119
18. [18]
  Zhongyan Cao , Youzhi Xu , Menghua Li , Xiao Xiao , Xianqiang Kong , Deyun Qian . Electrochemically Driven Denitrative Borylation and Fluorosulfonylation of Nitroarenes. University Chemistry, 2025, 40(4): 277-281. doi: 10.12461/PKU.DXHX202407017
19. [19]
  Yonghui ZHOU , Rujun HUANG , Dongchao YAO , Aiwei ZHANG , Yuhang SUN , Zhujun CHEN , Baisong ZHU , Youxuan ZHENG . Synthesis and photoelectric properties of fluorescence materials with electron donor-acceptor structures based on quinoxaline and pyridinopyrazine, carbazole, and diphenylamine derivatives. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 701-712. doi: 10.11862/CJIC.20230373
20. [20]
  Feng Zheng , Ruxun Yuan , Xiaogang Wang . “Research-Oriented” Comprehensive Experimental Design in Polymer Chemistry: the Case of Polyimide Aerogels. University Chemistry, 2024, 39(10): 210-218. doi: 10.12461/PKU.DXHX202404027

Get Citation

PDF

XML

Metrics

PDF Downloads(2)
Abstract views(680)
HTML views(86)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142