Alcoholysis of Epoxides and Aziridines Catalyzed by  Quaternary Ammonium Bisulfate

Chin. J. Org. Chem. ›› 2009, Vol. 29 ›› Issue (05): 794-797. Previous Articles Next Articles

Reports

硫酸氢季铵盐催化环氧化物和氮杂环丙烷的醇解反应

张万轩* ; 叶康; 刘丽琴曹锰

(湖北大学有机功能分子合成与应用教育部重点实验室武汉 430062)

收稿日期:2008-08-01 修回日期:2008-11-03 发布日期:2009-05-20
通讯作者: 张万轩

Alcoholysis of Epoxides and Aziridines Catalyzed by Quaternary Ammonium Bisulfate

Zhang, Wanxuan*; Ye, Kang; Liu, Liqing; Cao, Meng

(Key Laboratory for the Synthesis and Application of Organic Functional Molecules, Ministry of Education,
Hubei University, Wuhan 430062)

Received:2008-08-01 Revised:2008-11-03 Published:2009-05-20
Contact: Zhang, Wanxuan

Abstract

Tetrabutylammonium bisulfate (TBAHS) and macroporous resin (D201)-supported quaternary ammonium bisulfate (D201-HSO4) were used as catalysts in ring-opening reactions of epoxides and aziridines with al-cohols respectively, and high yields of corresponding β-alkoxy alcohols or β-alkoxy amines were obtained. These two catalysts were both efficient in the reactions, but the resin-supported quaternary ammonium bisulfate (D201- HSO4) was more convenient for preparation and recycling.

Key words: polymer-supported catalyst, aziridi, alcoholysis, epoxide, quaternary ammonium bisulfate

Cite this article

Zhang, Wanxuan*; Ye, Kang; Liu, Liqing; Cao, Meng. Alcoholysis of Epoxides and Aziridines Catalyzed by Quaternary Ammonium Bisulfate[J]. Chin. J. Org. Chem., 2009, 29(05): 794-797.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

[1]	Zuliang Chen, Yingjing Wei, Junliang Zhang. Recent Advances in Cycloaddition Reactions of Donor-Acceptor Aziridines via Carbon-Carbon Bond Cleavage [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3078-3088.
[2]	Xiaoyu Lu, Xiaomei Sun, Yaqing Niu, Junchao Wang, Wenjing Yin, Mengting Gao, Zi Liu, Zhenghuan Wei, Tinghua Tao. Copper-Catalyzed Decarboxylative Cross-Coupling of α‑Fluoroacrylic Acids with N-Tosyl Oxaziridines [J]. Chinese Journal of Organic Chemistry, 2023, 43(6): 2110-2119.
[3]	Erjun Hao, Xiaobo Ding, Kexin Wang, Honghao Zhou, Qiliang Yang, Lei Shi. Recent Progress on [3+2] Ring-Expansion Reaction of Aziridines with Unsaturated Compounds [J]. Chinese Journal of Organic Chemistry, 2023, 43(12): 4057-4074.
[4]	Liangcai Yao, Jinghan Gui. Application of the Radical Polyene Cyclization Reaction in Natural Product Synthesis [J]. Chinese Journal of Organic Chemistry, 2022, 42(9): 2703-2714.
[5]	Qingfeng Du, Lu Zhang, Feng Gao, Le Wang, Wanbin Zhang. Progress in Transition Metal-Catalyzed Asymmetric Ring-Opening Reactions of Epoxides and Aziridines [J]. Chinese Journal of Organic Chemistry, 2022, 42(10): 3240-3262.
[6]	Peng Wang, Da Yang, Huan Liu. Recent Advances on the Synthesis of β-Lactams by Involving Carbon Monoxide [J]. Chinese Journal of Organic Chemistry, 2021, 41(9): 3448-3458.
[7]	Gucheng Yuan, Jiawei Liu, Shihang Yu, Chaonan Yuan, Qinghua Bian, Min Wang, Jiangchun Zhong. Asymmetric Synthesis of (3Z,6Z,9S,10R)-9,10-Epoxy-3,6-heneicosadiene, Sex Pheromone Component of Hyphantria cunea [J]. Chinese Journal of Organic Chemistry, 2021, 41(11): 4437-4443.
[8]	Feng Liu, Jie Dai, Xu Cheng. Aryl-Iodide-Mediated Electrochemical Aziridination of Electron-Deficient Alkenes [J]. Chinese Journal of Organic Chemistry, 2021, 41(10): 4014-4020.
[9]	Wu Yali, Zhou Xuesong, Xiao Wenjing, Chen Jiarong. Recent Progress in Applications of Vinylaziridines in Organic Synthesis [J]. Chinese Journal of Organic Chemistry, 2020, 40(11): 3760-3776.
[10]	Liu, Quanyao, Shi, Lei, Liu, Ning. Pyridine Bridged Organocatalyst for the Synthesis of 3-Aryl-2-oxazolidinones from Carbon Dioxide, Terminal Epoxide, and Aryl Amine [J]. Chinese Journal of Organic Chemistry, 2019, 39(10): 2882-2891.
[11]	Sun Yunkai, Zhang Jin, Liu Huijun, Wang Xiaofeng. Synthesis and Polymerization of Optically Active Epoxides with Diazafluorenyl Substituent [J]. Chin. J. Org. Chem., 2018, 38(1): 253-258.
[12]	Zhu Chaoze, Feng Jianjun, Zhang Junliang. Rhodium(Ⅰ)-Catalyzed Stereospecific [3+2] Cycloadditions of Vinylaziridines and Ynamides [J]. Chin. J. Org. Chem., 2017, 37(5): 1165-1172.
[13]	Chu Xu, Chang Honghong, Gao Wenchao, Wei Wenlong, Li Xing. Research Progress in the Ring-Opening Reactions of Aziridines by Carbon Nucleophiles [J]. Chin. J. Org. Chem., 2017, 37(10): 2569-2589.
[14]	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]. Chin. J. Org. Chem., 2017, 37(1): 116-121.
[15]	Huang Yaobing, Yang Tao, Liu Anfeng, Zhou Xincheng, Pan Hui. Microwave-Assisted Alcoholysis of Cellulose to Methyl Levulinate Catalyzed by SnCl₄/H₂SO₄ [J]. Chin. J. Org. Chem., 2016, 36(6): 1438-1443.

硫酸氢季铵盐催化环氧化物和氮杂环丙烷的醇解反应

Alcoholysis of Epoxides and Aziridines Catalyzed by Quaternary Ammonium Bisulfate

PDF

Knowledge

Cited

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments