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Leuckart–Wallach反应

浏览:51 日期:06-17 11:18


酮和胺在过量的甲酸作为还原剂的条件下进行还原胺化的反应。当用醛作为底物的反应为Eschweiler–Clarke还原胺化反应。


反应机理

胺先亲核进攻酮生成胺基醇,脱水得到亚胺离子中间体,甲酸还原得到产物


反应实例





Leuckart–Wallach反应后通过Wagner-Meerwein迁移进行分子内的胺基迁移得到产物。


参考文献

1. Leuckart, R. Ber. 1885, 18, 2341-2344. Carl L. R. A. Leuckart (1854-1889) was born in Giessen, Germany. After studying under Bunsen, Kolbe, and von Baeyer, he became an assistant professor at Göttingen. Unfortunately, chemistry lost a brilliant contributor by his sudden death at age 35 as a result of a fall in his parent’s house.【Carl L. R. A. Leuckart (1854-1889)生于德国吉森, 后来师从于 Bunsen, Kolbe, 和von Baeyer,称为哥根廷大学副教授,可惜在35岁意外死亡,对于化学界是巨大的损失。

2. Wallach, O. Ann. 1892, 272, 99. Otto Wallach (1847-1931), born in Königsberg, Prussia, studied under Wöhler and Hofmann. He was the director of the Chemical Institute at Göttingen from 1889 to 1915. His book “Terpene und Kampfer” served as the foundation for future work in terpene chemistry. Wallach was awarded the Nobel Prize in Chemistry in 1910 for his work on alicyclic compounds.【Otto Wallach (1847-1931)生于普鲁士的哥尼斯堡,师从于Wöhler 和 Hofmann。在1889年到1915年出任哥根廷大学化学研究所大学主任。他所著的《萜烯和樟脑》为后来萜烯化学奠定了基础。Wallach由于在脂环化合物方面的研究获得了1910年的诺贝尔化学奖。

3. Moore, M. L. Org. React. 1949, 5, 301-330. (Review).

4. DeBenneville, P. L.; Macartney, J. H. J. Am. Chem. Soc. 1950, 72, 3073-3075.

5. Lukasiewicz, A. Tetrahedron 1963, 19, 1789-1799. (Mechanism).

6. Bach, R. D. J. Org. Chem. 1968, 33, 1647-1649.

7. Musumarra, G.; Sergi, C. Heterocycles 1994, 37, 1033-1039.

8. Martínez, A. G.; Vilar, E. T.; Fraile, A. G.; Ruiz, P. M.; San Antonio, R. M.; Alcazar, M. P. M. Tetrahedron: Asymmetry 1999, 10, 1499-1505.

9. Kitamura, M.; Lee, D.; Hayashi, S.; Tanaka, S.; Yoshimura, M. J. Org. Chem. 2002, 67, 8685-8687.

10. Brewer, A. R. E. Leuckart–Wallach reaction. In Name Reactions for Functional Group Transformations; Li, J. J., Ed.; Wiley: Hoboken, NJ, 2007, pp 451-455. (Review).

11. Muzalevskiy, V. M.; Nenajdenko, V. G.; Shastin, A. V.; Balenkova, E. S.; Haufe, G. J. Fluorine Chem. 2008, 129, 1052-1055.



编译Name Reactions (A Collection of Detailed Reaction Mechanisms), Jie Jack Li,  Leuckart–Wallach reactionpage 362-363.



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