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論文名稱 Title |
1. 芳香基甲基疊氮之熱解研究
2. 苯甲酸 3-(1-丙烯基)-2-噻吩甲酸酐之熱解研究
3. 芳香基亞胺之光解與熱解研究 1. Pyrolytic Study of Arylmethylazides 2. Pyrolytic Study of Benzoic 3-(1-Propenyl)-2-thiophenecarboxylic Anhydride 3. Pyrolytic and Photolytic Studies of Arylimine |
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系所名稱 Department |
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畢業學年期 Year, semester |
語文別 Language |
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學位類別 Degree |
頁數 Number of pages |
229 |
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研究生 Author |
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指導教授 Advisor |
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召集委員 Convenor |
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口試委員 Advisory Committee |
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口試日期 Date of Exam |
2006-06-23 |
繳交日期 Date of Submission |
2006-06-26 |
關鍵字 Keywords |
芳香基甲基疊氮、瞬間真空熱裂解、光化學、α-氧代-鄰-菎哢二甲烷、芳香基亞胺 photochemistry, arylimine, flash vacuum pyrolysis, arylmethylazides, α-oxo-ortho-quinodimethane |
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統計 Statistics |
本論文已被瀏覽 5735 次,被下載 15 次 The thesis/dissertation has been browsed 5735 times, has been downloaded 15 times. |
中文摘要 |
1. 以芳香基甲基疊氮化合物33b與34b進行熱解反應,可經由3,3- |
Abstract |
1. FVP of arylmethylazides (33b、34b) via 3,3-sigmatropic rearrangement gave nitrogen-containing heterocyclic compounds (2b、4b). FVP of 35 gave 3-benzyl-2-thiophenecarbaldehyde (65) by 1,2 H shift of nitrene 32 followed by hydrolysis. 2. FVP of benzoic 3-(1-propenyl)-2-thiophenecarboxylic anhydride (67) gave 7-hydroxybenzo[b]thiophene (70) and cyclopenteno[b]thiophene (71). Compound 71 is difficult to synthesize by normal organic synthetic methods. The formation of 7-hydroxybenzo[b]thiophene (70) suggesting the existence of 68. 3. FVP of arylimine gave phenanthridine (3)、3-methylpyrrolo[2,3-c] quinoline (69) and thieno[2,3-c]quinoline (134). Such a method can synthesize tricyclic products in one step. On the other hand, photolytic study of arylimine gave compounds 156、184、164、180、185 and 186. |
目次 Table of Contents |
第一章 芳香基甲基疊氮之熱解研究 壹、 緒論...............................................1 貳、結果與討論.........................................11 參、結論...............................................31 肆、實驗部份...........................................36 伍、參考文獻...........................................65 第二章 苯甲酸 3-(1-丙烯基)-2-噻吩甲酸酐之熱解研究 壹、 緒論..............................................69 貳、結果與討論.........................................88 參、結論...............................................96 肆、實驗部份...........................................97 伍、參考文獻..........................................100 第三章 芳香基亞胺之光解與熱解研究 壹、 緒論.............................................103 貳、結果與討論........................................111 參、結論..............................................176 肆、實驗部份..........................................180 伍、參考文獻..........................................212 |
參考文獻 References |
1.Wikel, J. H.; Denney, M. L.; Vasileff, R. T. J. Heterocyclic Chem. 1993, 289-296. 2.(a) Wikel, J. H.; Denney, M. L.; Vasileff, R. T. J. Heterocyclic Chem. 1984, 1135-1140. (b) Klemm, L. H.; Merrill,R. E.; Lee, F. H. W.; Klopfenstein, C. E. J. Heterocyclic Chem. 1974, 205-209. (c) Klemm, L. H.; Merrill,R. E. J. Heterocyclic Chem. 1974, 355-361. (d) Klemm, L. H.; Merrill,R. E.; Lee, F. H. W.; J. Heterocyclic Chem. 1974, 535-545. (e) Clementi, S.; Alunni, S.; Klemm, L. H. J. Chem. Soc., Perkin Trans. 2, 1976, 1135-1139. 3.(a) Klemm, L. H.; Klopfenstein, E.; Zell, R.; McCoy, D. R. Klemm, R. A. J. Org. Chem. 1969, 347-354. (b) Klemm, L. H.; Louris, J. N. J. Heterocyclic Chem. 1984, 785-789. 4.(a) Hibino, S. J. Org. Chem. 1984, 5006-5008. (b) Schneller, S. W.; Clough, F. W.; Hardee, L. E. J. Heterocyclic Chem. 1976, 273-275. (c) Popp, F. D.; Kant, J. J. Heterocyclic Chem. 1984, 1119-1120. 5.Taylor, E. C.; Macor, J. E. J. Org. Chem. 1987, 4280-4287. 6.Herz, W.; Tsai, L. J. Am. Chem. Soc. 1953, 5122-5123. 7.Dressler, M. L.; Joullié, M. M. J. Heterocyclic Chem. 1970, 1257-1268. 8.Kessar, S. V.; Singh, P.; Venugopal, D. J. Org. Chem. 1992, 57, 6716- 6720. 9.(a) Boit, H. G. Chem. Ber, 1954, 87, 1704. (b) Brossi, A.; Grethe, G.; Teitel, S.; Wildman, W. C.; Bailey, D. T. J. Org. Chem. 1970, 35, 1100-1104. (c) Brossi, A.; Teitel, S. J. Org. Chem. 1970, 35, 3559-3561. 10.(a) Aranapakam, V.; Albright, J. D.; Grosu, G. T.; Chan, P. S.; Coupet, J. Bioorg. Med. Chem. Lett. 1999, 9, 1733-1736. (b) Watthey, J. W. H.; Gavin, T.; Desai, M.; Finn, B. M,; Rodebaugh, R. K.; Patt, S. T. J. Med. Chem.1983, 26, 1116-1122. 11.Couture, A.; Deniau, E.; Woisel, P.; Grandclaudon, P.; Carpentier, J. F. Tetrahedron Lett. 1996, 37, 3697-3700. 12.Smolinsky, G.; Feuer, B. I. J. Org. Chem. 1966, 31, 3882-3884. 13.Kaba, E. P.; Abramovitch, R. A. J. Am. Chem. Soc. 1980, 735-740. 14.Chadwick, D. J.; Carpenter, A. J. Tetrahedron Lett. 1985, 26, 1777- 1780. 15.Gschwend, H. W.; Hamden, A. J. Org. Chem. 1975, 40, 2008-2009. 16.Joe, G. H.; Kim, S.; Do, J. Y. J. Am. Chem. Soc., 1994, 116, 5521-5522. 17.Toselli, M.; Zanirato, P. J. Chem. Soc. Perkin Trans. 1 1992, 9, 1101-1104. 18.Chadwick, D. J.; Carpenter, A. J. J. Chem. Soc. Perkin Trans. 1 1985, 2, 173-181. 19.Coates, R. M.; Ashburn, S. P. J. Org. Chem. 1985, 50, 3076-3081. 20.Hitchcock, S. A.; Pattenden, G. J. Chem. Soc. Perkin Trans. 1 1992, 11, 1323-1328. 21.Bonnaud, B.; Funes, P.; Jubault, N.; Vacher, B. Eur. J. Org. Chem. 2005, 15, 3360-3369. 22.Ibrahim, Y. A.; Al-Awadi, N. A.; Kual, K. Tetrahedron 2003, 59, 5425-5430. 23.Anastasiou, D.; Jackson, W. R. Aust. J. Chem. 1992, 45, 21-37. 24.Beugelmans, R.; Chastanet, J.; Roussi, G. Tetrahedron 1984, 40, 311-314. 25.Knochel, P.; Koradin, C.; Dohle, W.; Rodriguez, A. L.; Schmid, B. Tetrahedron 2003, 59, 1571-1588. 26.Cho, C. S.; Kim, J. H.; kim, T. J.; Shim, S. C. Tetrahedron 2001, 57, 3321-3330. 27.Liu, Y.; Gribble, G. W. Tetrahedron Lett. 2001, 42, 2949-2952. 28.MacDowell, D. W. H.; Jeffries, A. T. J. Org. Chem. 1971, 36, 1053-1055 1. Cava, M. P.; Napier, D. R. J. Am. Chem. Soc. 1957, 79, 1701-1705. 2. Cava, M. P.; Deana, A. A.; Muth, K. J. Am. Chem. Soc. 1959, 81, 6458-6460. 3. Spangler, R. J.; Kim, J. H. Tetrahedron Lett. 1972, 13, 1249-1251. 4. Spangler, R. J.; Beckmann, B. G,;Kim, J. H. J. Org. Chem. 1977, 42, 2989-2996. 5. Schiess, P.; Heizmann, M. Angew. Chem. Int. Ed. Engl. 1977, 16, 469-470. 6. Schiess, P.; Eberle, M.; Huys, F. M.; Wirz, J. Tetrahedron Lett. 1984, 21, 2201-2204. 7. Tamura, Y.; Wada, A.; Sasho, M.; Kita, Y. Tetrahedron Lett. 1981, 22, 4283-4286. 8. Tamura, Y.; Muhri, S.; Maeda, H.; Tsugoshi, T.; Sasho, M.; Kita, Y. Tetrahedron Lett. 1984, 25, 309-312. 9. Chou, C. H.; Wu, C. C.; Chen, W. K. Tetrahedron Lett. 1995, 36, 5065-5068. 10. Wentrup, C.; Bender, H.; Gross, G. J. Org. Chem. 1987, 52, 3838- 3847. 11. Kessar, S. V.; Singh, P.; Venugopal, D. J. Chem. Soc. Chem. Commun. 1985, 1258-1259. 12. Olofson, R. A.; Vander Meer, R. K.; Stournas, S.; Morrison, D. S. J. Org. Chem. 1984, 49, 3367-3372. 13. Kessar, S. V.; Singh, P.; Venugopal, D. J. Org. Chem. 1992, 57, 6716- 6720. 14. Kuzuya, M.; Miyake, F.; Okuda, T. Tetrahedron Lett. 1980, 21, 1043-1046. 15. Chapmann, O. L.; McIntosh, C. L.; Pacansky, J.; Calder, G. V.; Orr, G. J. Am. Chem. Soc. 1973, 95, 4061-4062. 16. 國立中山大學化學研究所研究生邱紹榕之博士論文,中華民國八十九年六月。 17. 國立中山大學化學研究所研究生曾本文之博士論文,中華民國八十四年六月。 18. 國立中山大學化學研究所研究生龔振裕之碩士論文,中華民國八十三年六月。 19. 國立中山大學化學研究所研究生詹承杰之碩士論文,中華民國八十四年六月。 20. De, A.; Ghosh, S. C.; Samanta, S. S. J. Chem. Soc. Perkin Trans. 1 1997, 14, 3673-3677. 21. Reinecke, M. G.; Newson, J. G.; Chen, L. J. J. Am. Chem. Soc. 1981, 103, 2760-2769. 1. (a) Suffness, M.; Cordell, G. A. The Alkaloids; Academic: New York, 1985; Vol. 25, pp 178-189. (b) Krane, B. D.; Fagbule, M. O.; Shamma, M. Gözler, B. J. Nat. Prod. 1984, 47, 1-43. 2. (a) Cordell, G. A.; Farnsworth, N. R. Heterocycles 1976, 4, 393-427. (b) Phillips, S. D.; Castle, R. N. J. Heterocycl. Chem. 1981, 18, 223-232. (c) Clenment, B.; Weide, M.; Wolschendorf, U.; Kock, I. Angew. Chem. Int. Ed. 2005, 44, 635-638. (d) Treus, M.; Estevez, J. C.; Castedo, L.; Estevez, R. J. Tetrahedron Lett. 2002, 43, 5323-5325. (e) Sotomayor, N.; Dominguez, E.; Lete, E. J. Org. Chem. 1996, 61, 4062-4072. (f) Nakanishi, T.; Suzuki, M.; Mashiba, A.; Ishikawa, K.; Yokotsuka, T. J. Org. Chem. 1998, 63, 4235-4239. (g) Nakanishi, T.; Suzuki, M.; Saimoto, A.; Kabasawa, T. J. Nat. Prod. 1999, 62, 864-867. (h) Nakanishi, T.; Suzuki, M. Org. Lett. 1999, 1, 985-988. 3. Mallory, F. B.; Wood, C. S.; Gordon, J. T. J. Am. Chem. Soc. 1964, 86, 3094-3102. 4. Badger, G. M.; Joshua, C. P.; Lewis, G. E. Tetrahedron Lett. 1964, 5, 3711-3713. 5. Mallory, F. B.; Wood, C. S. Tetrahedron Lett. 1965, 6, 2643-2648. 6. Thompson, C. M.; Docter, S. Tetrahedron Lett. 1988, 29, 5213-5216. 7. Caronna, T.; Gabbiadini, S.; Mele, A.; Recupero, F. Helv. Chim. Acta 2002, 85, 1-8. 8. Ho, T. I.; Wu, J. Y.; Wang, S. L. Angew. Chem. Int. Ed. 1999, 38, 2558-2560. 9. Plater, M. J. Tetrahedron Lett. 1994, 35, 801-802. 10.Ibrahim, Y. A.; Al-Awadi, N. A.; Kual, K. Tetrahedron 2003, 59, 5425-5430. 11. Núñez, A.; Sánchez, A.; Burgos, C.; Alvarez-Builla, J. Tetrahedron 2004, 60, 6217-6224. 12. Koradin, C.; Dohle, W.; Rodriguez, A. L. Schmid, B.; Knochel, P.Tetrahedron 2003, 59, 1571-1587. 13. Burgess, H.; Donnelly, J. A. Tetrahedron 1991, 47, 111-120. 14. (a) Sohl, W. E.; Shriner, R. L. J. Am. Chem. Soc. 1931, 53, 4168-4170. (b) Wiersum, U. E.; Jenneskens, L. W. Tetrahedron Lett. 1993, 34,6615-6618. 15. Patterson, J. M.; Mayer, C. F.; Smith, W. T. J. Org. Chem. 1975, 40, 1511-1514. 16. Arvela, R. K.; Leadbeater, N. E. J. Org. Chem. 2003, 68, 9122-9125. 17. Hayakawa, K.; Yodo, M.; Ohsuki, S.; Kanematsu, K. J. Am. Chem.Soc. 1984, 106, 6735-6740. 18. Wang, E. C.; Huang, K. S.; Chen, H. M.; Wu, C. C.; Lin, G. J. J. Chin.Chem. Soc. 2004, 51, 619-628. 19. Collins, M. J.; Hatton, P. M.; Sternhell, S. Aust. J. Chem. 1992, 45,1119-1134. 20. Loader, C. E.; Anderson, H. J. Can. J. Chem. 1981, 59, 2673-2676. 21. Padwa, A.; Gasdaska, J. R.; Tomas, M.; Turro, N. J.; Cha, Y.; Gould, I. R. J. Am. Chem. Soc. 1986, 108, 6739-6746. 22. Van Leusen, A. M.; Siderius, H.; Hoogenboom, B. E.; Van Leusen, D. Tetrahedron Lett. 1972, 13, 5337-5340. 23. Alberola, A. l; Ortega, A. G.; Sadaba, M. L.; Sanudo, C. Tetrahedron, 1999, 55, 6555-6566. 24. Elsom, L. F.; Alan Jones, R. J. Chem. Soc. B, 1970, 79-81. 25. Faust, R.; Weber, C.; Fiandanese, V.; Marchese, G.; Punzi, A. Tetrahedron, 1997, 53, 14655-14670. 26. Paudler, W. W.; Kress, T. J. J. Org. Chem. 1967, 32, 2616-2620. 27. Sutherland, R. G.; Zhang, C. H.; Piorko, A.; Lee, C. C. Can. J. Chem. 1989, 67, 137-142. 28. Yang, Y.; Hoernfeldt, A. B.; Gronowitz, S. J. Heterocycl. Chem. 1989,26, 865-868. 29. Hatsuda, M.; Seki, M. Tetrahedron, 2005, 61, 9908-9917. 30. Kourouli, T.; Kefalas, P.; Ragoussis, N.; Ragoussis, V. J. Org. Chem. 2002, 67, 4615-4618. 31. Van Tamelen, E. E.; Whitesides, T. H. J. Am. Chem. Soc. 1968, 90,3894-3896. 32. 國立中山大學化學研究所研究生陳秉樞之博士論文,中華民國八十六年六月。 33. Dumoulin, H.; Rault, S.; Robba, M. J. Heterocycl. Chem. 1996, 33, 255-258. 34. Hwu, J. R.; Tseng, W. N.; Patel, H. V.; Wong, F. F.; Horng, D. N.; Liaw, B. R.; Lin, L. C. J. Org. Chem. 1999, 64, 2211-2218. 35. Saito, S.; Hatanaka, K.; Yamamoto, H. Tetrahedron, 2001, 57, 875-887. 36. Imhof, W. J. Organomet. Chem. 1997, 533, 31-44. 37. Alcaide, B.; Almendros, P.; Salgado, N. R.; Martinez-Alcazar, M. P.; Hernandez-Cano, F. Eur. J. Org. Chem. 2001, 10, 2001-2010. |
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