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Chin. J. Org. Chem. ›› 2010, Vol. 30 ›› Issue (02): 266-271. Previous Articles Next Articles
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余开辉,张小丽,胡乔生,刘良先*
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Yu Kaihui Zhang Xiaoli Hu Qiaosheng Liu Liangxian*
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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
TU Kai-Hui, ZHANG Xiao-Li, HU Jiao-Sheng, LIU Liang-Xian. FeCl3 Reaction of Alkynols with Iodine: Convenient Synthetic Route to Iodocycloenol Ethers[J]. Chin. J. Org. Chem., 2010, 30(02): 266-271.
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