隨著環保意識的高漲，以具有揮發性低、不易燃及回收容易等特性的”綠色溶劑”－離子熔液來取代傳統有毒、揮發性高的有機溶劑是必然的趨勢。近年來，室溫離子熔液已被廣泛應用於合成反應中，並且已經可以達到與在一般有機溶劑中進行反應的同等效果甚至更佳。
　　本篇論文是將含有烷類取代的咪唑類化合物加入鹵化鋅配製成室溫離子熔液EMIC-ZnCl2、C8MIB-ZnBr2、C8C8IB-ZnBr2，其中包含手性結構的室溫離子熔液C5MIB-ZnBr2。利用這些熔液作為溶劑暨催化劑來進行Diels-Alder反應，並且探討鹵化鋅劑量、反應時間、產率、產物選擇性（endo/exo）的關係。其中EMIC-ZnCl2＝1：2的離子熔液對於環戊二烯與CH2＝CHC(O)R類型的親二烯基的反應，都有良好的產率和endo/exo比例大於10的產物選擇性。EMIC-ZnCl2＝1：2在環戊二烯與丙烯酸乙酯的反應，可以重複使用至少3次，而產率並無明顯減少的現象；但是手性室溫離子熔液對於產物的鏡像選擇性（enantiomeric excess）的效果不佳。

　　In the search for cleaner technologies for chemical synthesis finding alternatives to toxic volatile organic solvents is a particular important goal. Room temperature ionic liquids（RTIL）which are nonvolatile, inflammable, and good solvation power, have attracted a lot of recent attention as a “green solvent” alternative.

　　The use of RTIL as solvents for Diels-Alder reactions has been reported. In this thesis, RTILs（EMIC-ZnCl2、C8MIB-ZnBr2、C8C8IB-ZnBr2、chiral C5MIB-ZnBr2）form from 1,3-dialkylimidazolium halides and ZnX2 in 1：2 ratio are studied. We found that EMIC-ZnCl2 is air and moisture stable as solvent and Lewis acid catalyst leads to dramatic enhancements of rate and stereoselectivity. For example, the reactions between cyclopentadiene and dienophiles（ethyl acrylate、MVK）to give a mixture of endo and exo products in a ratio selectivity up to 10：1. At the end of the reaction the product also forms a separate phase on top of the ionic liquid and is easily separated then washing with a small amount of ethyl ehthr and chloroform, which then allows reuse of the ionic liquid catalyst. For example, the reaction between cyclopentadiene and ethyl acrylate could be repeated at least three times with no noticeable drop in activity or yield.

　　Further study to probe the effect of chiral functionalised ionic liquid C5MIB-ZnBr2 and such group with no significant entiomeric effect on the course of the Diels-Alder reactions.

（1）R. A. Sheldon, J. Chem. Technol. Biotechnol., 1997, 68, 381.

（2）A. A. Fannin, Jr., D. A. Floreani, L. A. King, J. S. Landers, B. J. Piersma, D. J. Stech, R. L. Vaughn, R. L. Wilkes, J. L. Williams, J. Phys. Chem., 1984, 88, 2614-2621.

（3）J. S. Wilkes, J. A. Levisky, R. A. Wilson, C. L. Hussey, Inorg. Chem., 1982, 21, 1263-1264.

（4）H. Stegemann, A. Rhode, A. Reiche, A. Schnittke, H. Füllbier, Electrochim. Acta, 1992, 37, 379-383.

（5）K. R. Seddon, J. Chem. Technol. Biotechnol., 1997, 68, 351-356.

（6）R. A. Sheldon, Chem. Commun., 2001, 2399-2407.

（7）R.Hagiwara, Y. Ito, J. Fluorine Chem., 2000, 105, 221-227.

（8）（a）P. Walden, Bull. Acad. Imper. Sci. (St. Petersburg), 1914, 1800.
　　（b）S. Sugden, H. Wilkins, J. Chem. Soc., 1929, 1291-1298.

（9）R. A. Osteryoung, Advances in Molten Salt Chemistry, G. Mamantov, C. Mamantov, Editors, Elsevier, New York, 1983 Vols. 5 and 6.

（10）（a）T. Welton, Chem. Rev., 1999, 99, 2071-2084.
　　　（b）J. Dupont, P. A. Z. Suarez, R. F. de Souza, Chem. Rev., 2002, 102, 3667-3692.

（11）（a）J. G. Huddleston, H. D. Willauer, R. D. Rogers, Chem. Commun., 1998, 1765-1766.
　　　（b）L. Shyu, Q. Zhang, Z. Zhang, WO200140150-A1, 2000.

（12）F. H. Hurley, T. P. Wier, J. Electrochem. Soc., 1951, 98, 203.

（13）J. S. Wilkes, J. A. Levisky, R. A. Wilson, C. L. Hussey, Inorg. Chem., 1982, 21, 1263.

（14）E. I. Cooper, E. J.M. O’Sullivan, “Proceedings of the eighth International Symposium of Molten Salts, Physical and High Temperature Materials Division Proceedings”, PV 92-16, NJ(1992).

（15）J. S. Wilkes, M. J. Zaworodtko, J. Chem. Soc., Chem. Commun., 1992, 13, 965.

（16）J. Dupont, P. A. Z. Suarez, R. F. de Souza, J.Chim. Phys., 1998, 95, 1626-1639.

（17）J. Fuller, R. T. Carlin, H. C. De Long, J. Chem. Soc., Chem. Commun,. 1994, 299-300.

（18）P. Bonhôte, A. P. Dias, N. Papageorgiou, K. Kalyanasundaram, M. Grätzeb, Inorg. Chem., 1996, 35, 1168.

（19）K. W. Street Jr., W. E. Acree Jr., J. C. Fetzer, P. H. Shetty, C. F. Poole, Appl. Spectrosc., 1989, 43, 1149.

（20）T. Soujanya, R. W. Fessenden, A. Samaten, J. Phys, Chem., 1996, 100, 3507.

（21）N. V. K. Sudhir, Chem. Commun., 2001, 413-414.

（22）S.-I. Hsiu, J.-F, Huang, I.-W, Sun, Electrochimica Acta, 2002, 47, 4367-4372.

（23）G. W. Parshall, J. Am. Chem. Soc., 1972, 94, 8716.

（24）C. E. Song, W. H. Shim, E. J. Roh, J. H. Choi, Chem. Commun., 2000, 1695.

（25）C. J. Adams, M. J. Earle, G. Roberts, K. R. Seddon Chem. Commun., 1998, 2097-2098.

（26）Y. Chauvin, L. Mussman, H. Olivier, Angew. Chem., Int. Ed. Engl. 1995, 34, 2698.

（27）J. Doupont, A. L. Monteiro, F. K. Zinn, R. F. De souza Tetradedron : Asymmetry 1997, 2, 177.

（28）Y. Chauvin, H. Olivier FR 95-14 147, 1995.

（29）C. E. Song, E. J. Roh Chem. Commun., 2000, 837.

（30）D. E. Kaufmann, M. Nouroozian, H. Henze Synlett 1996, 1091.

（31）K. R. Seddon, M. J. Earle, A. J. Carmichael Org. Lett. 1999, 1, 197.

（32）C. J. Mathews, P. J. Smith, T. Welton, Chem. Commun., 2000, 1249.

（33）M. J. Earle, P. B. McCormac, K. R. Seddon, Green Chem. 2000, 2, 261.

（34）T. Fischer, T. Sethi, T. Welton, Tetrahedron Lett, 1999, 40, 793-796.

（35）D. A. Jaeger, C. E. Tucker, Tetrahedron Lett, 1989, 30, 1785-1788.

（36）D. Huchette, B. Thery, F. Petit, J. Mol. Catal 1978, 4, 433.

（37）M. Onaka, P. Yamasaki, Chem. Lett. 1998, 259.

（38）C. W. Lee, Tetrahedron Lett, 1999, 40, 2461.

（39）J. M. Fraile, C. Cativiela, J. I. Garcia, J. Catal., 1992, 137, 394.

（40）K. Maruoka, A. B. Concepcion, Bull. Chem. Soc. Jpn., 1992, 65, 3501-3503.

（41）J. R. Sanders, “An Investigations of Transport properties and Ion Association in Room Temperature Haloaluminate Molten Salt”, Ph.D. Dissertation, The University of Mississipi（1987）.

（42）S. V. Dzyuba, R. A. Bartsch, J. Heterocyclic. Chem. 2001, 38, 265.

（43）R. W. McCabe, O. L. Parri, A. H. Price, J. Mater. Chem. 1993, 3, 609.