杏耀总代平台_Zimmerman重排

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杏耀总代平台_Zimmerman重排

1,4-二烯类化合物在光照条件下转化为烯基环丙烷的反应。也被称为双-π-甲烷重排( Di-π-methane rearrangement)。


反应机理

在光照下,碳碳双键发生π-π跃迁生成双自由基中间态,然后重排生成光化学重排产物。

反应实例

杏耀总代平台_Zimmerman重排

杏耀总代平台_Zimmerman重排

参考文献

1. (a) Zimmerman, H. E.; Grunewald, G. L. J. Am. Chem. Soc. 1966, 88, 183–184. Howard E. Zimmerman (1926–2012) was a professor at the University of Wisconsin at Madison. He is also known for the Traxler–Zimmerman trasition state for the asymmetric synthesis. (b) Zimmerman, H. E.; Armesto, D. Chem. Rev. 1996, 96, 3065–3112. (Review). (c) Zimmerman, H. E.; Církva, V. Org. Lett. 2000, 2, 2365–2367.

2. Armesto, D.; Horspool, W. M.; Langa, F.; Ramos, A. J. Chem. Soc., Perkin Trans. I 1991, 223–228.

3. Jiménez, M. C.; Miranda, M. A.; Tormos, R. Chem. Commun. 2000, 2341–2342.

4. Ünaldi, N. S.; Balci, M. Tetrahedron Lett. 2001, 42, 8365–8367.

5. Altundas, R.; Dastan, A.; Ünaldi, N. S.; Güven, K.; Uzun, O.; Balci, M. Eur. J. Org. Chem. 2002, 526–533.

6. Zimmerman, H. E.; Chen, W. Org. Lett. 2002, 4, 1155–1158.

7. Tanifuji, N.; Huang, H.; Shinagawa, Y.; Kobayashi, K. Tetrahedron Lett. 2003, 44, 751–754.

8. Dura, R. D.; Paquette, L. A. J. Org. Chem. 2006, 71, 2456–2459.

9. Singh, V.; Chandra, G.; Mobin, S. M. Synlett 2008, 2267–2270.

10. Cox, J. R.; Simpson, J. H.; Swager, T. M. J. Am. Chem. Soc. 2013, 135, 640–643.

编译自:Name Reactions (A Collection of Detailed Reaction Mechanisms), Jie Jack Li, Zimmerman rearrangementpage 654-655.

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