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完整後設資料紀錄
DC 欄位 | 值 | 語言 |
---|---|---|
dc.contributor.advisor | 劉緒宗 | |
dc.contributor.author | Bei-Sih Liao | en |
dc.contributor.author | 廖倍偲 | zh_TW |
dc.date.accessioned | 2021-06-13T01:10:17Z | - |
dc.date.available | 2008-07-30 | |
dc.date.copyright | 2007-07-30 | |
dc.date.issued | 2007 | |
dc.date.submitted | 2007-07-23 | |
dc.identifier.citation | 參 考 文 獻
1. Lewis, G. N.”Valency and Structure of Atoms and Molecules”; Wiley: New York, 1923. 2. Lindström, U. M. Chem. Rev. 2002, 102, 2751-2772. 3. (a)Manabe K.; Mori Y. ; Wakabayashi T.; Nagayama S.; Kobayashi, S.J. Am. Chem. Soc. 2000, 122, 7202-7207. (b) Manabe, K.; Kobayashi, S. Tetrahedron Lett. 1999, 40, 3773-3776. 4. Paquette, L. A. Ed. ”Encyclopedia of reagents for organic synthesis” John & Sons : Chichester, New Acid in Organic Synthesis, 1995. 5. Manabe, K.; Kobayashi, S. Acc. Chem. Res. 2002, 35, 209-217. 6. Kobayashi, S.; Wakabayashi T.; Nagayama S.; Oyamada, H.Tetrahedron Lett. 1997, 38, 4559-4562. 7. Kobayashi, S.; Wakabayashi T.Tetrahedron Lett. 1998, 39, 5389-5392. 8. Strauss, S. H. Chem. Rev. 1993, 93,927-942. 9. (a) Suzuki,H.; Tachimori,S.Phys. Chem. Chem. Phys. 2003, 5, 726-733. (b) Morawetz, H. Adv. Catal. 1969, 20,341-348 (c) Fendler, J. H.; Fendler, e. J. catalysis Micellar and Macromolecular systems, Academic Press, New York, 1975 10. Cordes, E. H.; Dunlap, R. B. Acc.Chem.Res. 1969, 2, 329-335. 11. (a) Kobayashi, S.; Hachiya, I.J. Org. Chem. 1994, 59, 3590-3596. (b) Kobayashi, S.; Hachiya, I.; Yamanoi, Y. Bull. Chem. Soc, Jpn. 1994, 67, 2342. (c) Kobayashi, S.;Hachiya, I.;Araki, M.;Ishitani, H. Tetrahedron Lett. 1993, 34, 3755. 12. Chang, C. T.; Chen, C. L. ;Liu, Y. H. ;Peng, S. M.; Chou, P. T.; Liu, S. T.Inorg. Chem. 2006, 45, 7590-7592. 13. (a) Leatherman, M. D.; Svejda, S. A.; Johnson, L. K.; Brookhart, M.J. Am. Chem. Soc. 2003, 125, 3068-3081. (b) Brookhart, M.; Grant, B.;Volpe, A. F. J. Organometallics 1992, 11, 3920-3926. (c) Golden, J. H.; Mutolo, P. F.; Lokovsky, E. B.; Disalvo, F. J. Inorg. Chem. 1994, 33, 5374-5375. 14. Buschmann, W. E.; Miller, J.S. Chem. Eur. J. 1998, 9,1731-1737. 15. Battal, T.; Siswanto, C.; Rathman, J. F. Langmuir 1997, 13, 6053-6057 16. Shiraki, Y.; Ontsuka, K.; Takuma, K.; Sonoda, T.; Kobayashi, H. Bull. Chem. Soc, Jpn. 1985, 58, 3041-3046. 17. Baeyer, A.; Emmerling, A. Chemische Berichte 1869, 2, 679-685. 18. (a) Van Orden, R. B.; Lindwell, H. G. Chem. Rev. 1942, 30, 69-96. (b) Robinson, B. Chem. Rev. 1963, 63, 373-401. (c) Robinson, B. Chem. Rev. 1969, 69, 227-250. 19. Heaney, H.; Ley, S. V. Organic Syntheses, 1974, 54, 58-63. 20. James, P. N.; Snyder, H. R.Organic Syntheses, 1959,39, 30-37. 21. (a) Gregorovich, B. V.; Liang, K.; Clugston, M.; Macdonald, S. Can. J. Chem. 1968, 46, 3291-3298. (b) Roomi, M.; Macdonald, S. Can. J. Chem. 1970, 48, 139-147. (c) Auria, M. Tetrahedron 1991, 47, 9225-9232. 22. (a) Chatterjee, A.; Manna, S.; Benerji, J.; Pascard, C.; Prange, T.; Shoolery, J. J. Chem.Soc., Perkin Trans. 1 1980, 553-559. (b) Noland, W. E.; Venkiteswaran, M. R.; Richards, C. G. J. Org. Chem. 1961, 26, 4241-4248. (c) Wang, Y. M.; Wen, Z.; Chen, X. M.; Du, D. M.; Matsuura, T.; Meng, J. B. J. Heterocycl. Chem. 1998, 35, 313-319. (d) Yadav, J. S.; Reddy, B. V. S.; Mueth, C. V. S. R.; Kumar, G. M.; Madan, C. Synthesis 2001, 783-789. 23. Zhang, Z.-H.; Yin, L ; Wang, Y.-M. Synthesis 2005, 12, 1949–1954. 24. Mo, L.-P.; Ma, Z.-C.; Zhang, Z.-H. Synth. Commun. 2005, 35,1997–2004. 25. Babu, G.; Sridhar, N.; Perumal, P. T. Synth. Commun. 2000, 30, 1609–1614. 26. Ji, S.-J.; Zhon, M.-F.; Gu, D.-G.; Wang, S. Y.; Loh, T.-P. Synlett 2003, 2077–2079. 27. (a) Chen, D. P.; Yu, L. B.; Wang, P. G. Tetrahedron Lett. 1996, 37, 4467-4470.(b) Nagarajan, R.; Perumal, P. T.Tetrahedron 2002, 58, 1229-1232. (c) Mi, X. L.; Luo, S. Z.; He, J.Q.; Chen, J. P. Tetrahedron Lett. 2004, 45, 4567-4570. 28. (a) Yadav, J. S.; Reddy, B. V.S.; Sunitha, S. Adv. Synth. Catal. 2003, 345-349. (b) Ji, S. J.; Zhou, M. F.; Gu, D. G.; Jiang, Z. Q.; Loh, T. P. Eur. J. Org. Chem. 2004, 1584-1587. (c) Bandgar, B. P.; Shaikh, K. A. Tetrahedron Lett. 2003, 44, 1959-1961.(d) Chakrabarfy, M.; Ghosh, N.; Basak, R.; Harigaya, Y. Tetrahedron Lett. 2002, 43, 4075-4078.(e) Koshima, H.; Matsusaka, W. J. Heterocycl. Chem. 2002, 39, 1089-1094. (f) Chen, D. P.; Yu, L. B.; Wang, P. G. Tetrahedron Lett. 1996, 37, 4467-4470. (g) Wang, L. M.; Han, J. W.; Tian, H.; Sheng, J.; Fan, Z. Y.; Tang, X. P. Synlett 2005, 337-343. (h) Vijender, R. A.; Ravinder, K.; Niranjan, R. V. L.;Venkateshwer, G. T.; Ravikanth, V.; Venkateswarlu, Y. Synth Commun. 2003, 33, 3687-3693. 29. Tanabe, K.; H¨olderich, W.F.; Appl. Catal. A: Gen. 181 (1999) 399. 30. Nagarajan, R.; Perumal, P. T. Chem. Lett. 2004, 33, 288–289. 31. (a) Chakrabarty, M.; Gosh, N.; Basak, R.; Harigaya, Y. Tetrahedron Lett. 2002, 43, 4075–4078. (b) Penieres-Carrillo, G.; Garcı´a-Estrada, J. G.; Gutie´rrez- Ramı´rez, J. L.; Alvarez-Toledano, C. Green Chem. 2003, 5, 337–339. 32. Bandgar, B. P.; Shaikh, K. A. Tetrahedron Let. 2003, 44, 1959–1961 33. Koshima, H.; Matsuaka, W. J. Heterocycl. Chem. 2002, 39, 1089–1091. 34. Ramesh, C.; Ravindranath, N.; Das, B. J. Chem. Res. Synop. 2003, 72–74. 35. Teimouri, M.B.; Mivehchi, H. Synth. Commun. 2005, 35, 1835–1843. 36.(a) Ojima, I.; Inaba, S.; Yoshida, K. Tetrahedron Lett. 1977, 3643-3647. (b) Ojima, I.; Inaba, S.; Nagai, M. Synthesis 1981, 545-551. 37. Manabe, K.; Hamada, T.; Kobayashi, S. J. Am. Chem. Soc. 2002, 124, 5640-5641. 38. Hamada, T; Manabe, K.; Kobayashi, S.Chem. Eur. J. 2006, 12, 1205 – 1215 39. (a) Biginelli, P. Ber. 1891, 24, 1317 & 2962;(b) Kappe, C.O. Tetrahedron 1993, 49, 6937; (c) Lu, J.; Yang, B.; Bai,Y.; Ma, H. Chin. Org. Chem. 2001, 21, 640. 40. Atwal, K. S.; Rovnyak, G. C.; Schwartz, J.; Moreland, S.; Hedberg, A.; Gougoutas, J. Z.; Malley, M. F.; Floyd, D. M. J. Med. Chem. 1990, 33, 1510–1515. 41. Hu, E.; Sidler, D.R.; Dolling, U.-H. J. Org. Chem. 1998, 63, 3454-3457. 42. Reddy, C. V.; Mahesh, M.; Raju, P. V. K.; Ramesh Babu, T.;Narayana Reddy, V. V. Tetrahedron Lett. 2002, 43, 2657–2659. 43. Ranu, B. C.; Hajra, A.; Jana, U. J. Org. Chem. 2000, 65,6270–6272. 44. Fu, N.-Y.; Yuan, Y.-F.; Cao, Z.; Wang, S.-W.; Wang, J.-T.;Peppe, C. Tetrahedron 2002, 58, 4801–4807. 45. (a) Ma, Y.; Qian, C.; Wang, L.; Yang, M. J. Org. Chem. 2000, 65, 3864–3868. (b) Wang, L.; Qian, C.; Tian, H.; Ma, Y. Synth. Commun. 2003, 33, 1459–1468. (c) Dondoni, A.; Massi, A.; Minghini, E.; Sabbatini, S.; Bertolasi, V. J. Org. Chem. 2003, 68, 6172–618 46. Lu, J.; Bai, Y.; Wang, Z.; Yang, B.; Ma, H. Tetrahedron Lett. 2000, 41, 9075- 9078. 47. (a) Folkers, K.; Johnson, T. B. J. Am. Chem. Soc. 1933, 55, 2886-2893.(b) Folkers, K.; Johnson, T. B. J. Am. Chem. Soc. 1933, 55, 3784-3848. (c) Yadav, J. S.; Reddy, B. V. S.; Reddy, E. J.; Ramalingam, T. J. Chem. Res. 2000, 7, 354-360. 49. Lu, J.; Ma, H. Synllett 2000, 63-64. 50. (a) Cepanec, I.; Litvic´, M.; Bartolincˇic´ A.; Lovric, M. Tetrahedron 2005, 61, 4275–4280. (b) Salehi, H.; Guo, Q.-X. Synth. Commun. 2004, 34, 171-179. (c) Suzuki, I.; Suzumura, Y.; Takeda, K. Tetrahedron Lett. 2006, 47, 7861–7864. 51. Huang, Y.; Yang, F.; Zhu, C. J. Am. Chem. Soc. 2005, 127, 16386-16387. 52. Nino, A.D.; Maiuolo, L.; Nardi, M.; Procopio, A.; Tagarelli, A. Synthesis 2004, 4, 496-498. 53. Ji, H.-B. Eur. J. Org. Chem. 2003, 3659-3662. 54. Black, D. S.; Craig, D. C.; Santoso, M. Tethedron Let. 1999, 40, 6653-6656. 55. Li, W. J.; Lin, X. F.; Wang, J.; Li, G .L.; Wang, Y. G. Synthetic Communications 2005, 35, 2765–2769. 56. Mo, L. P.; Ma, Z. C.; Zhang, Z. H. Synthetic Communications 2005, 35, 1997–2004. 57. Teimouri, M. B.; Mivehchi, H. Synthetic Communications 2005, 35, 1835–1843. 58. Ji, S. J.; Zhou, M. F.; Gu, D. G.; Jiang, Z. Q.; Loh, T. P. Eur. J. Org. Chem. 2004, 1584-1587. 59. Singh, P. R.; Singh, D. U.; Samant, S. D. Synthetic Communications 2005, 35, 2133–2138. 60. Koshima, H.; Matsusaka, W. J. Heterocycl. Chem. 2002, 39 1089-1092. 61. Nair, V.; Abhilash, K. G.; Vidya, N. Org. Lett. 2005, 26, 5857-5859. 62. Koshima, H.; Matsusaka, W. J. Heterocycl. Chem. 2002, 39 1089-1092. 63. Yadav, J. S.; Reddy, B. V. S.; Murthy, C. V. S. R.; Kumar, G. M.; Madan, C. Synthesis. 2001, 5, 783–787. 64. D'Auria, M. Tetrahedron 1991, 47, 9225-9230. 65. Rajitha, B.; Reddy, P. N.; Kumar, B. S.; Sreenivasulu, N.; Reddy, Y.; Reddy, T. J. Chem. Res. Synop. 2005, 4, 222-223. 66. Reddy, A. V.; Ravinder, K.; Reddy, V. L. N.; Goud, T. V.; Ravikanth, V.; Venkateswarlu, Y. Synth. Commun. 2003, 33, 3687-3694. 67. Ke, B.; Qin, Y.; Wang, Y.; Wang, F. Synth. Commun. 2005, 35, 1209 -1212. 68. Yadav, J. S.; Reddy, B.V. S.; Murthy, C. V. S. R.; Kumar, G. M.; Madan, C. Synthesis, 2001, 5, 783-787. 69. Novak. T. J.; Kramer, D. N.; Klapper, H.; Daasch, L. W.; Murr, B. L. J. Org. Chem. 1976, 41, 870-875. 70. Ji, S. J.; Wang, S.Y.; Zhanga, Y.; Lohb, T. P. Tetrahedron 2004, 60, 2051–2055. | |
dc.identifier.uri | http://tdr.lib.ntu.edu.tw/jspui/handle/123456789/29555 | - |
dc.description.abstract | 摘 要
M(上標 n+)(BAr(上標 F)4)(上標-)(下標 n) [M = 鋰、鈉、鉀、銫、鎂、鈣、銀、鎳、鋅,ArF= 3,5-(trifluoromethyl)bromobenzene ] 在水溶液中,能進行酸催化的反應。金屬離子除了具有路易士酸的特性外,在陰離子的協助下,經由與水配位後,也能產生氫離子(H+),扮演布羅斯特酸的角色。 因此,M(上標 n+)(BAr(上標 F)4)(上標-)(下標 n)利用酸的性質可以催化聚合、水解縮醛、Mannich reaction、Biginelli reaction及合成bsindoles的反應,並得到不錯的效果。而屬於弱配位的陰離子(BAr(上標 F)4)(上標 -),在水溶液中會造成相轉移的現象,利用所形成微胞的系統,可使催化反應能順利的進行,並有效地縮短反應時間與降低反應溫度。 此論文中係利用M(上標 n+)(BAr(上標 F)4)(上標-)(下標 n)在水中進行不同類型的催化反應,不僅克服傳統路易士酸,如AlCl3、TiCl4、BF3.OEt2等,必須在無水狀態下進行催化的缺點,並減少有機溶劑的使用,使其儼然成為新一代的有機金屬催化試劑。 | zh_TW |
dc.description.abstract | Abstract
Metal salts, M(superscript n+)(Bar(superscript F)4)(superscript -)(subscript n) [M = Li、Na、K、Cs、Mg、Ca、Ag、Ni、Zn,ArF= 3,5-(trifluoromethyl)bromobenzene ], were prepared and employed as acid catalysts in aqueous medium. In addition to the Lewis acid property of metal ions, the hydrated metal ions associated with the tetraarylborate act as good Bronsted acid in water. Therefore, using these metal salts in catalyzing various reactions, such as preparation of bisindoles、Mannich reaction、Biginelli reaction、hydrolysis of acetal is investigated. In fact, the anion [(BAr(superscript F)4)(superscript-)] plays an important role in catalysis. In water, metal salts of tetrakis[3,5-di(trifluoromethyl)phenyl]borate and organic substrates would form a colloidal dispersion during the reaction. The emulsion appeared to accelerate the reaction. These metal salts could be as catalysts and surfactants to promote various reaction in a micellar system. Thus condensations or hydrolysis proceeded immediately under high concentration within the micelle. This procedure offers several advantages for the preparation of various organic compounds such as mild conditions, low loading of catalyst, high yields and in aqua medium, which make it a useful and attractive methodology for organic synthesis. | en |
dc.description.provenance | Made available in DSpace on 2021-06-13T01:10:17Z (GMT). No. of bitstreams: 1 ntu-96-R94223075-1.pdf: 9516752 bytes, checksum: d15b68a717b830d29ebb855a772c84dd (MD5) Previous issue date: 2007 | en |
dc.description.tableofcontents | 目 錄 I
圖目錄 III 表目錄 V 摘要(中文) VI 摘要(英文) VII 第一章 序論 1 1-1 酸催化在水中的應用 1 1-2 Lewis acid-surfactant-combined Catalysts (LASC)催化系統 2 1-3 微胞系統(Micellar systems)的特性 6 1-4 Mn+(BArF4)-n在水中的催化反應 8 1-5 研究目的 11 第二章 金屬鹽類的合成與其在催化反應的現象 12 2-1 Mn+(BArF4)-n[M=Li, Na, K, Cs, Mg, Ca, Ag, Ni, Zn]的合成 12 2-2 Mn+(BArF4)-n金屬離子的探討 14 2-3 Mn+(BArF4)-n在催化反應中的現象 20 第三章 Mn+(BArF4)-n催化合成 bisindoles化合物 22 3-1 Indole的特性與合成上的應用 22 3-2 溶劑效應與催化劑量的探討 23 3-3 金屬離子與陰離子對於催化反應的影響 28 3-4 金屬鹽類合成不同取代基的bisindoles化合物 32 第四章 Mn+(BArF4)-n 金屬鹽類應用於one-pot reaction及水解反應 37 4-1 Mannich type reaction 37 4-2 Biginelli reaction 44 4-3 催化縮醛水解反應 46 第五章 催化合成tetraindolyl(terephthalyl)dimethanes及其化合物之應用 50 5-1 金屬鹽類催化合成tetra-indole類化合物 50 5-2 tetraindolyl(terephthalyl)dimethanes的溶劑效應 53 5-3 teraindoles化合物對酸物質的偵測 54 第六章 結論 59 第七章 實驗部份 61 7-1 測試儀器 60 7-2 反應試劑與溶劑的前處理 62 7-3 實驗步驟 62 附錄 75 參考文獻 96 | |
dc.language.iso | zh-TW | |
dc.title | 弱配位金屬鹽類[M(上標 n+)(BAr(上標 F)4)(上標-)(下標 n)]在酸催化的應用 | zh_TW |
dc.title | Applications of Weakly Coordinated Metal Salts [M(superscript n+)(Bar(superscript F)4)(superscript -)(subscript n)]in Acid Catalysis | en |
dc.type | Thesis | |
dc.date.schoolyear | 95-2 | |
dc.description.degree | 碩士 | |
dc.contributor.coadvisor | 陳竹亭 | |
dc.contributor.oralexamcommittee | 周善行 | |
dc.subject.keyword | 酸催化,弱配位, | zh_TW |
dc.subject.keyword | Acid Catalysis,Weakly Coordinated, | en |
dc.relation.page | 100 | |
dc.rights.note | 有償授權 | |
dc.date.accepted | 2007-07-23 | |
dc.contributor.author-college | 理學院 | zh_TW |
dc.contributor.author-dept | 化學研究所 | zh_TW |
顯示於系所單位: | 化學系 |
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