本論文主要目的在研究具有β-丙二烯支鏈之α-碘基酮的離子性環化反應。利用本實驗室所發展的1,4-加成碘化方法製備出具有β-丙二烯支鏈之α-碘基酮化合物為起始物，以三氯化鋁媒介誘導及所外加碘正離子活化不飽和之丙二烯支鏈進行離子性環化反應。但是由於分離上的不易，經一連串的證明後確定沒有環化產物，推測是結構上的因素，只發生加成反應。

In this thesis, we study on the ionic iodo carbocyclization of the α-iodocycloalkanones bearing a β-allenyl side chain. β-Allenyl substituted-α-iodocycloalkanones were prepared from 2-cyclohexenones by 1,4-addition and trapped as silyl enol ethers, then added in the mixture of NaI and m-CPBA afforded the α-iodocycloalkanones as starting materials. We use aluminum chloride and iodonium source to induce the ionic iodo carbocyclization. Because of the difficulty of separation, we did many experiments in order to prove that whether we got cyclized products or not. We supposed it may be the structure factor caused the reason why we didn’t get the cyclized products but only the addition products were observered.

1.Lewis acids in Organics Synthesis; Yamamoto, H., Ed.; Wiley-VCH: New York, 2000.
2.Sha, C.-K.; Lee, F.-C.; Lin, H.-H. Chem. Commun. 2001, 39.
3.(a) Sha, C.-K.; Lin, H.-H.; Chang, W.-S.; Luo, S-.Y. Org. Lett. 2004, 6, 3289. (b) 林耿誼，碩士論文，國立清華大學，2003。 (c) 林穎瑞，碩士論文，國立清華大學，2004。
4.(a) Taguchi, T.; Kitagawa, O.; Inoue, T.; Hirano, K. J. Org. Chem. 1993, 58, 3106. (b) Taguchi, T.; Kitagawa, O.; Inoue, T. Tetrahedron Lett. 1992, 33, 2167. (c) Taguchi, T.; Kitagawa, O.; Inoue, T. Tetrahedron Lett. 1994, 35, 1059. (d) Taguchi, T.; Kitagawa, O.; Inoue, T.; Kurumizawa, S.; Ochiai, O. Tetrahedron Lett. 1995, 36, 1479.
5.Toru, T.; Kawai, S.; Uedo, Y. Synlett. 1996, 539.
6.(a) Taguchi, T.; Kitagawa, O.; Suzuk, T.; Inoue, T. Tetrahedron Lett. 1998, 39, 7357. (b) Taguchi, T.; Kitagawa, O.; Suzuk, T.; Inoue, T.; Watanabe, Y. J. Org. Chem. 1998, 63, 9470.
7.Yang, D.; Gao, Q.; Lee, C-S. Org. Lett. 2002, 4, 3271.
8.Taguchi, T.; Kitagawa, O.; Suzuk, T.; Fujiwara, H. Tetrahedron Lett. 1999, 40, 2549.
9.Taguchi, T.; Kitagawa, O.; Suzuk, T.; Fujiwara, H.; Shiro, M. J. Org. Chem. 2000, 65, 6819.
10.(a) Haszeldine, R. N.; Leedham, K.; Steele, B. R. J. Chem. Soc. 1954, 2040. (b) Hehre, W. J.; Stewart, R. F.; Pople, J. A. J. Chem. Phys. 1969, 51, 2657. (c) Dupuis, M.; Spangler, D.; Wendolowski. J. Nat. Resor. Comput. Chem. Software Cat. 1980, 1, program No. QG01.
11.Clive, D. L. J.; Joussef, A. C. J. Org. Chem. 1990, 55, 1096.
12.李芳城，博士論文，國立清華大學，2004。