一、2-雙甲基胺基二苯乙烯及其衍生物進行瞬間真空熱解反應，經由脫去甲基自由基及關環反應生成喹啉、1-甲基吲哚、3-苯基喹啉和3-苯基吲哚(3-phenylindole)，進行光解反應則會經由電子環化反應可得到1-雙甲基胺基菲、菲、2-(4-甲氧基苯基)-1-甲基-1H-喹啉-4-酮及(1-甲基-1H-吲哚-2-基)苯基甲烷酮。2,4'-二甲氧基二苯乙烯進行光解反應並加入酸性溶液，經由電子環化反應和[1,9]氫轉移可得到1,6-二甲氧基菲、1-甲氧基菲和酮類化合物。
二、 2-(2-氯基乙烯基)吡啶經由瞬間真空熱解法可得到苯駢[f]喹啉、苯駢[h]喹啉，若以4-(2-氯基乙烯基)吡啶當作起始物，經由瞬間真空熱解法可得到不同結構的苯駢[h]喹啉。

一、Flash vacuum pyrolysis (FVP) of 2-dimethylaminostilbene and its derivatives via elimination of methyl radical followed by cyclization gave quinoline and 1-methylindole and 3-phenylquinoline and 3-phenylindole. On the other hand, Photolysis of 2-dimethylaminostilbene and its derivatives via electrocyclization gave 1-dimethylaminophenanthrene, phenanthrene, 2-(4-methoxy-phenyl)-1-methyl-1H-
quinolin-4-one and 1-methyl-1H-indol-2-yl)phenylmethanone. Photolysis of 2,4'-dimethoxystilbene in acidic sulotion gave 1,6-dimethoxypheanthrene and 1-methoxypheanthrene and ketone compound via electrocyclization followed by [1,9] hydrogen shift.
二、FVP of 2-(2-chlorostyryl)pyridine gave benzo[f]quinolin, benzo[h]quinolin, on the other hand, FVP of 4-(2-chlorostyryl)pyridine gave different benzo[h]quinolin.

第一章 鄰位-雙甲基胺基苯乙烯基芳香環與其衍生物之熱解與光解研究
壹、緒論…………………………………………………1
貳、結果與討論…………………………………………16
參、結論…………………………………………………44
肆、實驗部份……………………………………………48
伍、參考文獻……………………………………………91

第二章2-氯基苯乙烯基吡啶之熱解研究
壹、緒論…………………………………………………94
貳、結果與討論…………………………………………101
參、結論…………………………………………………108
肆、實驗部份……………………………………………111
伍、參考文獻……………………………………………120

附錄ㄧ：第一章光譜資料
附錄二：第二章光譜資料

伍、 參考文獻
1. Hammond, G. S.; Saltiel, J. J. Am. Chem. Soc. 1962, 84, 4983-4984.
2. Mallory, F. B.; Wood, C. S.; Gordon, J. T.; Lindquist, L. C.; Savitz, M. L. J. Am. Chem. Soc. 1962, 84, 4361-4362.
3. Kupchan, S. M.; Wormser, H. C. Tetrahedron Lett. 1965, 6, 359-363.
4. Lewis, F. D. Acc. Chem. Res. 1979, 12, 152-158.
5. (a) Lewis, F. D.; Ho. T.-I.; Simpson, J. T. J. Am. Chem. Soc. 1982, 104, 1924-1929. (b) Yasuda, M.; Isami, T.; Kubo, J.-I.; Mizutani, M.; Yamashita, T.; Shima, K. J. Org. Chem. 1992, 57, 1351-1354.
6. Somers, J. B. M.; Couture, A.; Lablache-Combier, A.; Laarhoven, W. H. J. Am. Chem. Soc. 1985, 107, 1387-1394.
7. Loader, C. E.; Timmons, C. J. J. Chem. Soc. 1967, 1677-1681.
8. Turro, N. J.; Ramamurthy, V.; Cherry, W.; Farneth, W. Chem. Rev. 1978, 78, 125-145.
9. Saito, M.; Kamei, Y.; Kuribara, K.; Yoshioka, M. J. Org. Chem. 1998, 63, 9013-9018.
10. Turro, N. J.; Ramamurthy, V.; Cherry, W.; Farneth, W. Chem. Rev. 1978, 78, 125-145.
11. Saito, M.; Kamei, Y.; Kuribara, K.; Yoshioka, M. J. Org. Chem. 1998, 63, 9013-9018.
12. Huyser, E. S.; Neckers, D. C. J. Org. Chem. 1964, 29, 276-278.
13. (a) Ho, T.-I.; Ho, J.-H.; Wu, J.-Y. J. Am. Chem. Soc. 2000, 122, 8575-8576. (b) Ho, J.-H.; Ho, T.-I.; Liu, R. S. H. Org. Lett. 2001, 3, 409-411.
14. Larock, R. C.; Harrison, L. W. J. Am. Chem. Soc. 1984, 106, 4218-4227.
15. Arcadi, A.; Cacchi, S.; Marinelli, F. Tetrahedron Lett. 1992, 33, 3915.
16. Flynn, B. L.; Chaplin, J. H. Chem. Commun. 2001, 1594-1595.
17. (a) Flynn, B. L.; Hamel, E. Org. Lett. 2001, 3, 651-654. (b) Larock, R. C.; Yue, D. J. Org. Chem. 2002, 67, 1905-1909.
18. Flynn, B. L.; Hessian, K. O. Org. Lett. 2003, 5, 4377-4380.
19. Flynn, B. L.; Hessian, K. O.; Jung, M. K. Org. Lett. 2006, 8, 243-246.
20. 中山大學化學研究所研究生余品志之博士論文，中華民國九十六年十月。
21. Rodriguez, J. G.; Lafuente, A.; Martin-Villamil, R. J. Phys. Org. Chem. 2001, 14, 859-868.
22. Christoffers, J.; Frey, W.; Rosiak, A. Eur. J. Org. Chem. 2006, 4044-4054.
23. Flynn, B. L.; Hessian, K. O. Org. Lett. 2006, 8, 243-246.
24. Mallory, F. B.; Rudolph, M. J.; Oh, S. M. J. Org. Chem. 1989, 54, 4619.
25. Kon-Ya, K.; Shimidzu, N.; Miki, W.; Fndo, M. Biosci. Biotech. Biochem. 1994, 58, 2178-2181.
26. Ali, A. M.; Kondo, K.; Tsuda, Y. Chem. Pharm. Bull. 1992, 40(5), 1130-1136.
27. Kiddle, J. J. Tatrahedron Lett. 2000, 41, 1339-1341.
28. Shieh, R.-L.; Lin, R.-L.; Hwang, J.-J.; Jwo, J.-J. J. Chin. Chem. Soc. 1998, 45, 517-524.
29. Murahashi, S. I.; Yamamura, M.; Yanagisawa, K. I.; Mita, N.; Kondo, K. J. Org. Chem. 1979, 44, 2409-2417.
30. Alois Fu‥ rstner,; Mamane, V. J. Org. Chem. 2002, 67, 6264-6267.
31. Jesu′ s, E. de;Gordillo, A. I.; Lo′pez-Mardomingo, C. Org. Lett. 2006, 8, 3517-3520.
32. Ibrahim, Y. A.; Al-Awadi, N. A.; Kual, K. Tetrahedron 2003, 59, 5425-5430.
33. Zhu, J.; Jia, Y. J. Org. Chem. 2006, 71, 7826-7834.
34. Liu, Y.; Gribble, G. W. Tetrahedron Lett. 2001, 42, 2949-2952.
35. Ibrahim, Y. A.; Al-Awadi, N. A.; Kaul, K. Tetrahedron 2001, 57, 7377-7381.
36. Harrowven, D. C.; Guy, I. L.; Nanson, L. Angew. Chem. Int. Ed. 2006, 45, 2242 –2245.
37. Toyokuni, I.; Koyama, J.; Tagahara, K. Chem. Pharm. Bull. 1999, 47, 1038-1039.
38. Ishikura, M.; Terashima, M. J. Org. Chem. 1994, 59, 2634-2637.
39. Yang, Z.; Miao, H. Org. Lett. 2000, 2, 1765-1768.
伍、 參考文獻
1. Hammond, G. S.; Saltiel, J. J. Am. Chem. Soc. 1962, 84, 4983-4984.
2. Mallory, F. B.; Wood, C. S.; Gordon, J. T.; Lindquist, L. C.; Savitz, M. L. J. Am. Chem. Soc. 1962, 84, 4361-4362.
3. Kupchan, S. M.; Wormser, H. C. Tetrahedron Lett. 1965, 6, 359-363.
4. Lewis, F. D. Acc. Chem. Res. 1979, 12, 152-158.
5. (a) Lewis, F. D.; Ho. T.-I.; Simpson, J. T. J. Am. Chem. Soc. 1982, 104, 1924-1929. (b) Yasuda, M.; Isami, T.; Kubo, J.-I.; Mizutani, M.; Yamashita, T.; Shima, K. J. Org. Chem. 1992, 57, 1351-1354.
6. Somers, J. B. M.; Couture, A.; Lablache-Combier, A.; Laarhoven, W. H. J. Am. Chem. Soc. 1985, 107, 1387-1394.
7. Loader, C. E.; Timmons, C. J. J. Chem. Soc. 1967, 1677-1681.
8. Turro, N. J.; Ramamurthy, V.; Cherry, W.; Farneth, W. Chem. Rev. 1978, 78, 125-145.
9. Saito, M.; Kamei, Y.; Kuribara, K.; Yoshioka, M. J. Org. Chem. 1998, 63, 9013-9018.
10. Plater, M. J. Tetrahedron Lett. 1994, 35, 801-802.
11. 中山大學化學研究所研究生許躍騰朱立澤之博士論文，中華民國 九十五年六月。
12. (a) 中山大學化學研究所研究生余品志之博士論文，中華民國九十六年十月 (b) 中山大學化學研究所研究生江秋南之碩士論文，中華民國九十六年六月。
13. Hopf, H.; Dix, I.; Doll, C.; Jones, P. G. Eur. J. Org. Chem. 2002, 2547-2556.