自第一個穩定的咪唑鹽化合物被發現之後，很多相關的研究皆在探討其基本化學特性及催化上的應用，特別是在均相的反應上。
在我們的研究上，我們首先合成烯醇氮異環碳咪唑鹽化合物，之後再利用氧化銀將烯醇氮異環碳咪唑鹽化合物去氫化而得到化合物2。而化合物2類型之銀咪唑鹽類可進而在大氣中形成穩定的化合物。我們也可進一步簡單且廣泛的利用2去做金屬交換反應。銅咪唑鹽類可成功的製造經由銀咪唑鹽類進行金屬置換反應得到。
一系列不同官能基之胺類基團化合物被應用在異氰酸鹽催化環化三聚合反應。反應機制過程的細節可經由NMR 及X-ray 繞射實驗說明。經由環化三聚合反應而得到了一個非預期化合物7，証明氮異環碳化合物在反應時與兩個異氰酸鹽互相影響進而被脫去形成惰性物質。在結論中，我們發展有效分離free NHC carbenes的方法。並且，我們也發現在不同側邊臂官能基的NHC carbenes 會有不同的反應性及特性。

Since the first stable N-Heterocyclic carbene is found, there are many work done on exploring its basic chemical properties and catalysis application, in particularly the homogeneous reaction.
In our research, we first synthesized an enolate-NHC imidazolium which is subsequently deprotonated by Ag2O. This type of silver-NHC 2 is formed a stable compound forward lab atmosphere. Easy to synthesis and widely used to transfer metal has become its advantage. Copper-NHC is also successfully prepared through the transmetallation process via silver carbine 2.
A series of functional amino pendant linked N-Heterocyclic carbene complexes were prepared and employed as organic catalyst for isocyanate cyclotrimerization process. The detail of the mechanism process was elucidated through NMR spectroscopy and X-ray diffraction experiment. The cyclotrimerization unexpectedy 7, NHC containing double isocyanate interaction was isolated and found to be inactive species. In conclusion, we develop a more efficient method to isolate the free NHC carbenes. Moreover, we also show the different substutient functional pendant linked N-Heterocyclic carbene accompany with different reactivity and characteristic.

Chapter 5 Reference
1. Hahn, F. E.; Jahnke, M. C. Angew. Chem. lnt. Ed. 2008, 47, 3122-3172.
2. H.W. Wanzlick, H. J. Kleiner, Angew. Chem. 1961, 73, 493.
3. H.W. Wanzlick, H. J. Schonherr, Angew. Chem. lnt. Ed. 1968, 7, 141-142.
4. K. Ofele, J. Organomet. Chem. 1968, 12, 42.
5. A.J. Arduengo, R.L. Harlow, M.A. Kline, J. Am. Chem. Soc, 1991, 113, 361-363.
6. Herrmann, W. A.; Kohlpaintner, C. W. Angew. Chem., Int. Ed. Engl. 1993, 32, 1524-1544.
7. Herrmann, W. A. Angew. Chem., Int. Ed. 2002, 41, 1290–1309.
8. N-Heterocyclic Carbenes in Synthesis; Nolan, S. P. Ed.; Wiley-VCH: Weinheim, 2006.
9. Matthew D. M, Joseph M. D, and Paul R. H. Chem. Rev. 2004, 104, 2239-2258.
10. Shih, W. C.; Wang, C. H.; Chang, Y. T.; Glenn, P. A. Yap.; Ong, T.-G. Organometallics 2009, 28, 1060–1067.
11. H. Aihara, T. Matsuo and H. Kawaguchi. Chem. Commun., 2003, 2204.
12. B. E. Ketz, X. G. Ottenwaelder and R. M. Waymouth, Chem. Commun., 2005,
5693-5695.
13. Jered C. Garrison; Wiley J. Youngs. Chem. Rev. 2005, 105, 3978-4008.
14. H. A. Duong, M. J. Cross, and J. Louie. Org. Lett., 2004, 6, 4679–4681
15. B E. Ketz, A. P. Cole, and R. M. Waymouth, Organometallics 2004, 23, 2835-2837
16. Arnold, P. L.; Mungur, S. A.; Blake, A. J.; Wilson, C. Angew. Chem., Int. Ed. 2003, 42, 5981–5984.
17. Tulloch, A. A. D.; Danopoulos, A. A.; Winston, S.; Kleinhenz, S.; Eastham, G. J. Chem. Soc., Dalton Trans. 2000, 4499.
18. Pytkowicz, J.; Roland, S.; Mangeney, P. J. Organomet. Chem. 2001, 631, 157.
19. Bonnet, L. G.; Douthwaite, R. E.; Hodgson, R.; Houghton, J.; Kariuki, B. M.; Simonovic, S. Dalton Trans. 2004, 3528.
20. (a) Arduengo, A. J.; Harlow, R. L.; Kline, M. J. Am. Chem. Soc. 1991, 113,361–363. (b) Arduengo, A. J.; Dias, H. V. R.; Harlow, R. L.; Kline, M. J. Am. Chem. Soc. 1992, 114, 5530–5534.
21. Jong, H.; Patrick, B. O.; Fryzuk, M. D. Can. J. Chem. 2008, 86, 803–810.
22. (a) Kausamo, A; Tuononen, H. M.; Krahulic, K. E.; Roesler, R. Inorg. Chem. 2008, 47, 1145–1154. (b) Diez-Gonzalez, S.; Nolan, S. P. Coord. Chem. ReV. 2007, 251, 874–883.
23. Cowan, J. A.; Clyburne, J. A. C.; Davidson, M. G.; Harris, R. L. W.;
Howard, J. A. K.; Kupper, P.; Leech, M. A.; Richards, S. P. Angew. Chem. Int. Ed. 2002, 41, 1432–1434.