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有机化学
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有机化学 ›› 2009, Vol. 29 ›› Issue (01): 115-118. 上一篇    下一篇

研究简报

对甲苯磺酰氟/双氧水/碱体系和烯烃环氧化反应的研究

严兆华*,a ; 曾繁荣a ; 田伟生b ; 戴延凤a   

  1. (a南昌大学化学系 南昌 330031)
    (b中国科学院上海有机化学研究所 上海 200032)
  • 收稿日期:2008-04-02 修回日期:2008-08-20 发布日期:2009-01-20
  • 通讯作者: 严兆华

Epoxidation of Olefins with para-Toluenesulfonyl Fluoride/Hydrogen Peroxide/Base System

Yan, Zhaohua*,a; Zeng, Fanronga; Tian, Weishengb; Dai, Yanfenga   

  1. (a Department of Chemistry, Nanchang University, Nanchang 330031)
    (b Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032)
  • Received:2008-04-02 Revised:2008-08-20 Published:2009-01-20
  • Contact: Yan, Zhaohua

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被引次数

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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

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.

Key words: p-toluenesulfonic peracid, p-toluenesulfonyl fluoride, olefin, epoxidation