研究生: |
戴志娟 |
---|---|
論文名稱: |
銠金屬之環戊烯酮合成研究 |
指導教授: |
葉名倉
Yeh, Ming-Chang |
學位類別: |
碩士 Master |
系所名稱: |
化學系 Department of Chemistry |
論文出版年: | 2004 |
畢業學年度: | 92 |
語文別: | 中文 |
論文頁數: | 117 |
中文關鍵詞: | Pauson-Khand Reaction 、銠金屬 |
英文關鍵詞: | Pauson-Khand Reaction, Rhodium |
論文種類: | 學術論文 |
相關次數: | 點閱:153 下載:5 |
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利用有機鋅銅試劑製備帶炔官能基之雙烯三鐵錯合物,再加入氧化劑(CAN)將鐵去錯合,可得C5位置帶炔之環己雙烯化合物。再以C5位置帶炔之環己雙烯化合物為起始物,在銠金屬的催化下進行Pauson-Khand 反應(PKR)。
上述起始物以數個串聯的亞甲基為側鏈,連接炔基和環戊雙烯。當起始物的側鏈為兩個亞甲基時,進行PKR可以得到預期的合環產物;而起始物的側鏈改為三個亞甲基時,進行PKR可以得到預期的合環產物,以及三環連結產物,這個意外的發現來自於起始物進行雙烯轉移後的PKR產物。
The addition of alkyne-functionalized zinc-copper reagents to iron cation gives (η4-cyclohexa-1,3-diene)Fe(CO)3 complexes with an alkyne-functionalized side-chain at C-5 position of the ring. Decomplexation of the complexes with diammonium cerium(IV) nitrate afforded cyclohexadienyne compound. The alkynyl-substituted cyclohexa-1,3-dienes underwent intramolecular cyclization using 1 mol% of Rh(I) and carbon monoxide.
The rhodium-catalyzed Pauson-Khand reaction (PKR) of cyclohexa-1,3-dienes containing two methylene carbons and an alkyne in a chain produced regular PKR products. Cyclohexadienynes bearing three methylene units and a aromatic ring at the alkyne afforded regular PKR products and angularly fused tricyclic compounds, which were derived from diene migration followed by the PKR process.
第五章 參考文獻
1. (a) Davis, F. A.; Sheppard, A. C. Tetrahedron Lett. 1989, 45, 5703.; (b) Davis, F. A.; Chen, B. C. Chem. Rev. 1992, 92, 919.
2. Knochel, P. J. Org. Lett. 2003, 5, 1059.
3. Takimoto, M.; Mori, M. J. Am. Chem. Soc. 2002, 124, 10008.
4. Loh, T. P.; Song, H. Y.; Zhou, Y. Org. Lett. 2002, 4, 2715.
5. Evans, P. A.; Robinson, J. E.; Baum, E. W.; Fazal, A. N. J. Am. Chem. Soc. 2002, 124, 8782.
6. Widenhoefer R. A.; Tao P. J. Am. Chem. Soc. 2001, 123, 11290.
7. Siriwardana, A. I.; Nakamura, I.; Yamamoto,Y. J. Org. Chem. 2004, 69, 3202.
8. Verboom, R. C.; Persson, B.A.; Bäckvall, J. E. J. Org. Chem. 2004, 69, 3102.
9. Park, K. H.; Jung, I. G.; Kim, S. Y.; Chung, Y. K. Org. Lett. 2003, 5, 4967.
10. Rozhkov, R. V.; Larock, R. J. Org. Chem. 2003, 68, 6314.
11. Wang, X.; Chakrapani, H.; Stengone, C. N.; Widenhoefer, R. A. J. Org. Chem. 2001, 66, 1755.
12. Takimoto, M.; Shimizu, K.; Mori, M. Org. Lett. 2001, 3, 3345.
13. (a) Cheng, C. H.; Huang, D. J.; Rayabarapu, D. K. Chem. Eur. J. 2000, 6, 3706. (b) Cheng, C. H.; Huang, D. J.; Sambaiah, T. New J. Chem. 1998, 22, 1147. (c) Cheng, C. H.; Rayabarapu, D. K.; Sambaiah, T. Angew. Chem. Int. Ed. Engl. 2001, 40, 1286.
14. Cheng, C. H.; Rayabarapu, D. K. J. Am. Chem. Soc., 2002, 124, 690.
15. Hartwig, J. F.; Pawlas, J.; Nakao, Y. J. Am. Chem. Soc., 2002, 124, 3669.
16. Tong, X.; Zhang, Z.; Zhang, X. J. Am. Chem. Soc. 2003, 125, 6370.
17. William, H. M.; Jian Zhang, C. S.; Lecher, T.; Frazier, L.; Maren P. Org. Lett. 2002, 4, 1981.
18. Khand, I. U.; Knox, G. R.; Pauson, P. L.; Watts, W. E. J. Chem. Soc. Perkin Trans. 1 1973, 977.
19. (a) Brummond, K. M.; Lu, J. J. Am. Chem. Soc. 1999, 121, 5087. (b) Pérez-Serrani, L.; Casarrubios, L.; Domínguez, G.; Pérez-Castells, J. Chem. Commun. 2001, 2602. (c) Chevliakov, M. V.; Montgomery, J. J. Am. Chem. Soc. 1999, 121, 11139. (d) Nomura, I.; Mukai, C. Org. Lett. 2002, 4, 4301. (e) Iura, Y.; Sugahara, T.; Ogasawara, K. Org. Lett. 2001, 3, 291.
20. Sugihara, T.; Yamada, M.; Yamaguchi, M.; Nishizawa, M. Synlett 1999, 771.
21. Sugihara, T.; Yamada, M.; Ban, H.; Yamaguchi, M.; Kaneko, C. Angew. Chem. Int. Ed. Engl. 1997, 1, 1187.
22. P′erez-Serrano, L.; Casarrubios, L.; Dominguez, G.; P′erez-Castells, J. Org. Lett. 1999, 1, 1187.
23. Anorbe, L.; Problador, A.; Dominguez, G.; P′erez-Castells, J. Tetrahedron Lett. 2004, 45, 4441.
24. Pauson, P. L.; Kerr, W. J.; McLaughlin, M.; Morrison, A. J. Org. Lett. 2001, 3, 2945.
25. Odesra, A.; Wu, C. J.; Madhushaw, R.J.; Wang, S. L.; Liu, R. S. J. Am. Chem. Soc. 2003, 125, 9610.
26. Sugihara, T.; Yamaguchi, M. Synlett 1998, 1384.
27. Belanger, D. B.; O’Mahony, D. J. R.; Livinghouse, T. Tetrahedron Lett. 1998, 39, 7637.
28. Hayashi, M.; Hashimoto, Y. Angew. Chem. Int. Ed. Engl. 2000, 39, 631.
29. Rivero, M. R.; Carretero, J. C. J. Org. Chem. 2003, 68, 2975.
30. Yamanaka, M.; Nakamura, E., J. Am. Chem. Soc. 2001, 123, 1703.
31. Krafft, M. E.; Bonaga, L. V. R. Angew. Chem. Int. Ed. Engl. 2000, 39, 3676.
32. Son, S. U.; Chung, Y. K. J. Org. Chem. 2000, 65, 6142.
33. Hicks, F. A.; Kablaoui, N. M.; Buchwald, S. L; J. Am. Chem. Soc. 1999, 121, 5881
34. Nigishi, E.; Holmes, S. J.; Tour, J. M.; Miller, J. A.; Cederbaum, F. E.; Swanaon, D. R.; Takahashi, T. J. Am. Chem. Soc. 1989, 111, 3336.
35. Hoye, T. R.; Surlano, J. A. Organometallics 1992, 11, 2044.
36. Brummond, K. M.; Lu, J.; Petersen, J. J. Am. Chem. Soc. 2000, 122, 4915.
37. Pearson, A. J.; Dubbert, R. A. Organometallics 1994, 13, 1656.
38. Kondo, T.; Suzuki, N.; Okada, T.; Mitsudo, T. J. Am. Chem. Soc. 1997, 119, 6187.
39. Chatani, N.; Morimoto, T.; Fukumoto, Y.; Murai, S. J. Am. Chem. Soc. 1998, 120, 5335.
40. Lluis, P.; Amadeu, L.; Francisco, C.; Elies, M.; Carles, M.; Josep, M. M. J. Am. Chem. Soc. 1992, 114, 10449.
41. Grigg, R.; Zhang, L.; Collard, S.; Keep, A. Chem. Commun. 2003, 1902.
42. Shibata, T.; Takagi, K. J. Am. Chem. Soc. 2000, 122, 9852.
43. Le, H. M. T. Ph. D. Dissertation. Princeton University. 1985.
44. Jeong, N.; Sung, B. K.; Choi, Y. K. J. Am. Chem. Soc. 2000, 122, 6771.
45. Evans, P. A.; Robinson, J. E. J. Am. Chem. Soc. 2000, 122, 6771.
46. Shibata, T.; Toshida, N.; Takagi, K. Org. Lett. 2002, 4, 1619.
47. Fuji, K.; Morimoto, T.; Tsutsumi, K.; Kakiuchi, K. Angew. Chem. Int. Ed. Engl. 2003, 42, 2409.
48. Park, K. H.; Son, S. U.; Chung, Y. K. Chem. Commun. 2003, 1898.
49. Park, K. H.; Jung, I. G.; Chung, Y. K. Org. Lett. 2004, 6, 1183.
50. Wender, P. A.; Croatt, M. P.; Deschamps, N. M. J. Am. Chem. Soc. 2004, 126, 5948.
51. Lee, S. I.; Park, J. H.; Chung, Y. K.; Lee, S. G. J. Am. Chem. Soc. 2004, 126, 2714.
52. Mukai, C.; Inagaki, F.; Yoshida, T.; Kitagaki, S. Tetrahedron Lett. 2004, 45, 4117.
53. Jeong, N.; Kim, D. H.; Choi, J. H. Chem. Commun. 2004, in press.
54. Kobayashi, T.; Koga, Y.; Narasaka, K. J. Organomet. Chem. 2001, 624, 73.
55. Wender, P. A.; Deschamps, N. M.; Gamber, G. G. Angew. Chem. Int. Ed. Engl. 2003, 42, 1853.
56. 廖經瑋, 國立台灣師範大學化學所, 碩士論文, 1996.
57. 許記敏, 國立台灣師範大學化學所, 碩士論文, 1993.
58. Yeh, M. C. P.; Tsao, W. C.; Ho, J. S.; Tai, C. C.; Chiou, D. Y.; Tu, L. H. Organometallics 2004, 23, 792.