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有机化学
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有机化学 ›› 2010, Vol. 30 ›› Issue (02): 266-271. 上一篇    下一篇

研究论文

FeCl3作用下的碘代醚化反应: 一种合成碘代环烯醚的方便方法

余开辉，张小丽，胡乔生，刘良先*   

  1. (赣南师范学院化学与生命科学学院 赣州 341000)
  • 收稿日期:2009-06-03 修回日期:2009-08-11 发布日期:2010-02-20
  • 通讯作者: 刘良先 E-mail:lxliu@xmu.edu.cn

FeCl3 Reaction of Alkynols with Iodine: Convenient Synthetic Route to Iodocycloenol Ethers

Yu Kaihui Zhang Xiaoli Hu Qiaosheng Liu Liangxian*   

  1. (Department of Chemistry and Biology, Gannan Teachers’ College, Ganzhou 341000)
  • Received:2009-06-03 Revised:2009-08-11 Published:2010-02-20

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对FeCl3作用下各种炔醇与碘的反应进行了详细研究, 结果表明在FeCl3和碘的作用下, 炔醇发生分子内碘代环化反应生成碘代环烯醚, 产率为63%～90%. 在相同的反应条件下, 炔丙醇类则生成邻二碘化物, 产率为15%～88%. 该反应具有操作简单、底物适应广、反应快(3 h)和碘用量(0.5 equiv.)少等特点, 是制备碘代环烯醚和2,3-二碘代烯醇的好方法.

关键词: 分子内碘代环醚化反应, 三氯化铁, 炔醇, 邻二碘代烯醇

The FeCl3-mediated reaction of alkynols with iodine resulted in intramolecular addition of hydroxyl to alkyne to produce a wide range of iodocycloenol ethers in good to excellent yields (63%～90%) under mild reaction conditions. On the other hand, 1,2-diiodides were obtained generally in good yields (15%～88%) when propargyl alcohols were reacted with iodine in the same condition. The advantages of our procedure include a decreased amount of iodine (0.5 equiv.) as well as short reaction time (3 h). The broad scope, mild reaction conditions, and experimental ease of this transformation have made it a valuable alternative to current available methods for the preparation of iodocycloenol ethers or 2,3-diiodoalkenols.

Key words: intramolecular iodoetherification, iron trichloride, alkynol, 2,3-diiodoalkenol