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-