Sommelet–Hauser重排
苄基季铵盐在氨基碱金属化合物的作用下得到铵叶立德中间体,接着进行[2,3]-Wittig重排生成邻甲基苄胺的反应。
反应机理
反应实例
参考文献
1. (a) Sommelet, M. Compt. Rend. 1937, 205, 56–58. (b) Kantor, S. W.; Hauser, C. R. J. Am. Chem. Soc. 1951, 73, 4122–4131. Charles R. Hauser (1900–1970) was a professor at Duke University.
2. Shirai, N.; Sato, Y. J. Org. Chem. 1988, 53, 194–196.
3. Shirai, N.; Watanabe, Y.; Sato, Y. J. Org. Chem. 1990, 55, 2767–2770.
4. Tanaka, T.; Shirai, N.; Sugimori, J.; Sato, Y. J. Org. Chem. 1992, 57, 5034–5036.
5. Klunder, J. M. J. Heterocycl. Chem. 1995, 32, 1687–1691.
6. Maeda, Y.; Sato, Y. J. Org. Chem. 1996, 61, 5188–5190.
7. Endo, Y.; Uchida, T.; Shudo, K. Tetrahedron Lett. 1997, 38, 2113–2116.
8. Hanessian, S.; Talbot, C.; Saravanan, P. Synthesis 2006, 723–734.
9. Liao, M.; Peng, L.; Wang, J. Org. Lett. 2008, 10, 693–696.
10. Tayama, E.; Orihara, K.; Kimura, H. Org. Biomol. Chem. 2008, 6, 3673–3680.
11. Zografos, A. L. In Name Reactions in Heterocyclic Chemistry-II, Li, J. J., Ed.; Wiley: Hoboken, NJ, 2011, pp 197–206. (Review).
12. Tayama, Eiji; Sato, Ryota; Takedachi, Keisuke; Iwamoto, Hajime; Hasegawa, Eietsu Tetrahedron 2012, 68, 4710–4718.
编译自:Name Reactions (A Collection of Detailed Reaction Mechanisms), Jie Jack Li, Sommelet–Hauser rearrangement,page 570-571.
相关反应介绍
[2,3]-Wittig重排
碱处理烯丙基醚重排得到高烯丙醇的反应,也被称为Still-Wittig重排。反应机理同Sommelet-Hauser重排类似。
反应机理
反应实例
参考文献
1. Cast, J.; Stevens, T. S.; Holmes, J. J. Chem. Soc. 1960, 3521-3527.
2. Thomas, A. F.; Dubini, R. Helv. Chim. Acta 1974, 57, 2084-2087.
3. Nakai, T.; Mikami, K.; Taya, S.; Kimura, Y.; Mimura, T. Tetrahedron Lett. 1981, 22,69-72.
4. Nakai, T.; Mikami, K. Org. React. 1994, 46, 105-209. (Review).
5. Kress, M. H.; Yang, C.; Yasuda, N.; Grabowski, E. J. J. Tetrahedron Lett. 1997, 38, 2633.
6. Marshall, J. A.; Liao, J. J. Org. Chem. 1998, 63, 5962-5970.
7. Maleczka, R. E., Jr.; Geng, F. Org. Lett. 1999, 1, 1111-1113.
8. Tsubuki, M.; Kamata, T.; Nakatani, M.; Yamazaki, K.; Matsui, T.; Honda, T. Tetrahedron:Asymmetry 2000, 11, 4725-4736.
9. Schaudt, M.; Blechert, S. J. Org. Chem. 2003, 68, 2913-2920.
10. Ahmad, N. M. [2,3]-Wittig Rearrangement. In Name Reactions for Homologations-Part II; Li, J. J., Ed.; Wiley: Hoboken, NJ, 2009, pp 241-256. (Review).
11. Everett, R. K.; Wolfe, J. P. Org. Lett. 2013, 15, 2926-2929.
编译自:Name Reactions (A Collection of Detailed Reaction Mechanisms), Jie Jack Li, [2,3]-Wittig rearrangement,page 638-639.