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(Hive Bee) 07-08-04 22:30 No 518225 |
Conversion of Alcohols to Alkyl Halides..... | |||||||
Immobilization of HX: [Hmim]X as Halogenating Agent, Recyclable Catalyst and Medium for Conversion of Alcohols to Alkyl Halides WU, Hai-Hong( ) SUN, Jing( ) YANG, Fan( ) TANG, Jie*( ) HE, Ming-Yuan( ) Chinese Journal of Chemistry, 2004, 22, 619 621 Abstract HX is immobilized by reaction of halogen acid with methylimidazole, and the formed ionic liquid [Hmim]X was used as halogenating agent, catalyst as well as medium for conversion of alcohols to alkyl halides. Excellent yields were obtained. The halides produced could be easily separated from the reaction mixture via simple decantation, and the ionic liquid [Hmim]X could be regenerated conveniently by adding equivalent of halogen acids followed by removal of water. Conclusion.... the halogen acid was immobilized in methylimidazole forming IL [Hmim]X. With the properties of Brønsted acidic acid, thermal stability and negligible vapor pressure, [Hmim]X could be used as halogenating agent, acidic catalyst as well as medium for conversion of alcohol to halide. It was very convenient to prepare and reuse all the time. The procedure is very practical for the preparation of primary and secondary halides. The studies on stereochemistry of the halogenation reactions are underway. References 1 (a) Larock, R. C. Comprehensive Organic Transformations, 2nd ed., John Wiley & Sons, New York, 1999, p. 689. (b) Guyer, A.; Bieler, A.; Hardmeier, E. Helv. Chim. Acta 1937, 20, 1462. (c) Vogel, A. J. Chem. Soc. 1943, 636. 2 (a) Norris, J. F.; Taylor, H. B. J. Am. Chem. Soc. 1907, 38, 627. (b) Nohrig, J. R.; Hammond, C. N.; Morrill, T. C.; Neckers, D. C. Experimental Organic Chemistry, W. H. Freeman and Company, New York, 1998, p. 369. 3 (a) Cole, A. C.; Jensen, J. L.; Ntai, I.; Tran, K. L. T.; Weaver, K. J.; Forbes, D. C.; Davis, Jr. J. H. J. Am. Chem. Soc. 2002, 124, 5962. (b) Huddleston, J. G.; Visser, A. E.; Reichert, W. M.; Willauer, H. D.; Broker, G. A.; Rogers, R. D. Green Chem. 2001, 3, 156. 4 Holbrey, J. D.; Seddon, K. R. J. Chem. Soc., Dalton Trans. 1999, 13, 2133. 5 Wasserscheid, P.; Keim, W. Angew. Chem., Int. Ed. 2000, 39, 3772. 6 Freemantle, M. Chem. Eng. News 2000, 15, 37. 7 Welton, T. Chem. Rev. 1999, 99, 2071. 8 (a) Du, D. M.; Chen, X.; Hua, W. T. Chin. J. Org. Chem. 2003, 23, 331 (in Chinese). (b) Yang, F.; Zhang, Y.-M.; Qiu, W.-W.; Tang, J.; He, M.-Y. Chin. J. Chem. 2002, 20, 114. (c) Zheng, R.; Yang, F.; Zou, G.; Tang, J.; He, M.-Y. Chin. J. Chem. 2003, 21, 1111. 9 Ren, R. X.; Wu, J. X. Org. Lett. 2001, 3, 3727. 10 Nguyen, H.-P.; Matondo, H.; Baboulene, M. Green Chem. 2003, 5, 303. 11 Zhu, H.-P.; Yang, F.; Tang, J.; He, M.-Y. Green Chem. 2003, 5, 38. Just hold on to the thread...that keeps us going http://www.chiapaslink.ukgateway.net/ |
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