| 研究生: |
曾昭明 Tseng, Chao-Ming |
|---|---|
| 論文名稱: |
溶劑效應對2-胺基-1,4-醌類化合物與羰基化合物之氧化性自由基反應的影響 The Role of Solvents in Oxidative Free Radical Reaction Initiated by Manganese (Ⅲ)Acetate Between 1,4-Quinone and Carbonyl Compounds |
| 指導教授: |
莊治平
Chuang, Che-Ping |
| 學位類別: |
碩士 Master |
| 系所名稱: |
理學院 - 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: | 89 |
| 中文關鍵詞: | 羰基化合物 、甲酸 、中性溶劑 、醋酸錳 |
| 外文關鍵詞: | free-radical, metals, oxidative cyclizations |
| 相關次數: | 點閱:93 下載:1 |
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最近30 年來,利用自由基進行環合反應已經在有機合
成中扮演著重要的角色。自由基反應的方法分為還原性與氧
化性自由基反應,可起始自由基的金屬也不盡相同;錳(Ⅲ)
是最廣泛使用於氧化性自由基反應的金屬,且其研究成果也
較完善。本篇報告將利用錳(Ⅲ)為起始氧化性自由基的金
屬,探討錳(Ⅲ)在不同溶劑中的表現。
本報告分為二個部分:第一部分是溶劑效應對2-胺基
-1,4-萘醌化合物、1,3-雙羰基化合物與醋酸錳(Ⅲ)的氧化
性自由基反應(式1、2、3、4)。第二部分是溶劑效應對2-
胺基-1,4-萘醌化合物、羰基化合物與醋酸錳(Ⅲ)的氧化性
自由基反應(式5、6、7)。
During the past 30 years, initiated cyclization by free-radical plays an important role for synthesis of cyclic compounds.There are two methods to produce free radical. First is reduction free-radical reaction, the other is oxidative free-radical reaction. The metals used in these reactions are also different. Commercially available Mn(OAc)3‧2H2O has been used for the majority
of oxidative cyclizations. In this report, we chose Mn(Ⅲ)as oxidant in our oxidative free-radical reaction.
There are two parts in this report. First one is solvent effect in oxidative free-radical reaction initiated by Mn(Ⅲ)between 2-amino-1,4-naphthoquinone and 1,3-dicarbonyl compounds(eq.1, eq.2, eq.3, eq.4). The other is solvent effect in oxidative free-radical reaction initiated by Mn ( Ⅲ ) between 2-amino-1,4-naphthoquinone and carbonyl compounds(eq.5,eq.6, eq.7).
1.Philippe Renaud; Mukund, P. Sibi. Radicals in Organic Sysnthesis, Vol. 1: Basic Principles, Wiley-Vch, 2001
2.Heiba, E. I.; Dessau, R. M. J. Org. Chem. 1974, 39, 3456.
3.Kende, A. S.; Koch, K. Tetrahedron Lett. 1986, 27, 6051.
4.Snider, B. B.; McCarthy, B. A. J. Org. Chem. 1993, 58, 6217.
5.Snider, B. B.; Cole, B. M. J. Org. Chem. 1995, 60, 5376.
6.Iwasawa, N.; Hayakawa, S.; Isobe, K.; Narasaka, K. Chem. Lett. 1991, 1193.
7.Iwasawa, N.; Funahashi, M.; Hayakawa, S.; Narasaka, K. Chem. Lett. 1993, 545.
8.Iwasawa, N.; Hayakawa, S.; Funahashi, M.; Isobe, K.; Narasaka, K. Bull. Chem. Soc. Jpn. 1993, 66, 819.
9.Masataka, I.; Yoshiki, K.; Chihiro, I.; Hiroshi, F.; Yoko, T.; Bastow, K. F.; Kou-Hsiung, L. J. Nat. Prod. 2000, 63(7), 893-897.
10.Moody, C. J. Synlett 1994, 681.
11.Yi, L. L.; Ting, C. C.; Cheng, C. C. J. Heterocycl Chem. 1996, 33, 113.
12.[a] Woodward, R. B.; Iacobucci, G. A. and Hochstein, F. A. J. Am. Chem. Soc. 1959, 81, 4434; [b] Kohn, K. W.; Ross, W. E. and Glaubiger, D. in Antibiotics, Vol 5, Part 2, Hahn, F. E., ed, Springer Verlag, Berlin, 1979, pp 195-213.
13.Juret, P.; Heron, H. F.; Couette, J. F.; Delozier, T.; LeTalaer, J. Y. Cancer Treat. Rep. 1982, 66, 1909.
14.Ducrocq, C.; Bisagni, E.; Rivalle, C. and Lhosta, J. M. J. Chem. Soc., Perkin Trans. 1. 1979, 142.
15.Larue, L.; Rivalle, C.; Muzard, G.; Paoletti, C.; Bisagni E.; Paoletti, J. J. Med. Chem. 1988, 31, 1951.
16.Jiang, M. C.; Chuang, C. P. J. Org. Chem. 2000, 65, 5409.
17.Tseng, C. C.; Wu, Y. L.; Chung, C. P. Tetrahedron, 2002, 58, 7625.
18. Wu, Y. L.; Chuang, C. P.; Lin, P. Y. Tetrahedron, 2001, 57, 5543.
19. Gemal, A. L.; Luche, J. L. J. Am. Chem. Soc. 1972, 103, 2888.
20. Booker-Milburn, K. I. Synlett 1992, 809.