Chin. J. Org. Chem. ›› 2010, Vol. 30 ›› Issue (02): 266-271. Previous Articles     Next Articles

Full Papers

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

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