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有机化学
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有机化学 ›› 1995, Vol. 15 ›› Issue (5): 530-535. 上一篇    下一篇

研究论文

2-苯基吲哚单重态氧反应机理

凌可庆;刘志滨;胡宏纹   

  1. 淮北煤炭师范学院化学系;中国科学技术大学应用化学系;南京大学化学系
  • 发布日期:1995-10-25

Mechanism of singlet oxygenation of 2-phenylindole

LIU ZHIBIN;HU HONGWEN   

  • Published:1995-10-25

被引次数

18

本文比较了在甲醇介质下, 2-苯基吲哚(1)单重态氧反应中的捕捉反应以及2-苯基-3H-吲哚-3-酮(4)的亲核加成反应特征。结果显示, 在1的单重态氧反应中, 捕捉反应主要发生于两性离子(2)阶段, 而4并非导致捕捉产物的重要中间体。根据上述事实, 结合有关反应溶剂极性效应的研究结果, 对反应机理进行了探讨。

关键词: 苯基吲哚, 吲哚 P, 反应机理, 单重态氧, 煤炭高校优秀青年科学基金, 亲核反应, 加成反应

Trapping reactions in singlet oxygenation of 2-phenylindole (1) and nucleophilic addition reactions of 2-phenyl-3H-indol-3-one (4) both in methanolic media were studied com-paratively. It was showed that trapping reactions in singlet oxygenation of 1 occured mainly on the stage of zwitterionic intermediate (2), whereas was not a major precursor to trapping prod-ucts. In views of such a conclusion as well as the observations on solvent polarity effect of the sin-glet oxygen reaction, a possible mechanism was proposed.

Key words: INDOLE P, REACTION MECHANISM, SINGLET OXYGEN, NUCLEOPHILIC REACTION, ADDITION REACTION

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