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| 对甲苯磺酰氟/双氧水/碱体系和烯烃环氧化反应的研究 | |
| 引用本文： | 严兆华,曾繁荣,田伟生,戴延凤.对甲苯磺酰氟/双氧水/碱体系和烯烃环氧化反应的研究[J].有机化学,2009,29(1):115-118. |
| 作者姓名： | 严兆华 曾繁荣 田伟生 戴延凤 |
| 作者单位： | 1. 南昌大学化学系,南昌,330031 2. 中国科学院上海有机化学研究所,上海,200032 |
| 摘 要： | 研究了对甲苯磺酰氟和双氧水在碱性条件下原位生成对甲苯过氧磺酸和烯烃尤其是富电子烯烃的环氧化反应的情况. 该氧化体系能将位阻较小的富电子烯烃环氧化, 并以良好的得率给出环氧化产物; 对位阻较大的富电子烯烃, 只以中等得率生成了环氧化产物. 它也能将α,β-不饱和酮环氧化. 实验结果进一步拓展了磺酰氟试剂在有机合成化学中的应用. |
| 关 键 词： | 对甲苯磺酰氟 对甲苯过氧磺酸 烯烃 环氧化 |
| 收稿时间： | 2008-4-2 |
| 修稿时间： | 2008-8-20 |
Epoxidation of Olefins with para-Toluenesulfonyl Fluoride/Hydrogen Peroxide/Base System |
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| Yan,Zhaohua,Zeng,Fanrong,Tian,Weisheng,Dai,Yanfeng.Epoxidation of Olefins with para-Toluenesulfonyl Fluoride/Hydrogen Peroxide/Base System[J].Chinese Journal of Organic Chemistry,2009,29(1):115-118. | |
| Authors: | Yan Zhaohua Zeng Fanrong Tian Weisheng Dai Yanfeng |
| Institution: | (a Department of Chemistry, Nanchang University, Nanchang 330031) (b Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032) |
| Abstract: | The epoxidation of olefins (especially for electron-rich olefins) with para-toluenesulfonic peroxy acid generated in situ from the reaction of para-toluenesulfonyl fluoride with hydrogen peroxide in the presence of base was investigated. On treatment with para-toluenesulfonyl fluoride/hydrogen peroxide/sodium hydroxide system, sterically less hindered electron-rich olefins were epoxidized to give the corresponding epoxides in high yields, while the sterically hindered electron-rich olefins in medium yields. α,β-Unsaturated ketone was also epoxidized in a high yield by this system. |
| Keywords: | p-toluenesulfonyl fluoride p-toluenesulfonic peracid olefin epoxidation |
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