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de Mayo反应2019-04-02

烯酮和烯烃进行[2 + 2]-光化学环加成后,进行反-羟醛缩合得到1,5-二酮的反应。

反应机理


底物头对尾排列进行环加成得到主要产物。


底物头对头排列进行环加成得到少量的异构体。

反应实例



参考文献

1. (a) de Mayo, P.; Takeshita, H.; Sattar, A. B. M. A. Proc. Chem. Soc., London 1962,119. Paul de Mayo received his doctorate from Sir Derek Barton at Birkbeck College, University of London. He later became a professor at the University of Western Ontario in London, Ontario, Canada, where he discovered the de Mayo reaction.[Paul de Mayo在伦敦大学伯贝克学院Derek Barton门下获得博士学位,后来出任加拿大西安大略大学教授,在那里他发现了de Mayo反应] (b) Challand, B. D.; Hikino, H.; Kornis, G.; Lange, G.; de Mayo, P. J. Org. Chem. 1969, 34, 794-806.

2. de Mayo, P. Acc. Chem. Res. 1971, 4, 41-48. (Review).

3. Oppolzer, W.; Godel, T. J. Am. Chem. Soc. 1978, 100, 2583-2584.

4. Oppolzer, W. Pure Appl. Chem. 1981, 53, 1181-1201. (Review).

5. Kaczmarek, R.; Blechert, S. Tetrahedron Lett. 1986, 27, 2845-2848.

6. Disanayaka, B. W.; Weedon, A. C. J. Org. Chem. 1987, 52, 2905-2910.

7. Crimmins, M. T.; Reinhold, T. L. Org. React. 1993, 44, 297-588. (Review).

8. Quevillon, T. M.; Weedon, A. C. Tetrahedron Lett. 1996, 37, 3939-3942.

9. Minter, D. E.; Winslow, C. D. J. Org. Chem. 2004, 69, 1603-1606.

10. Kemmler, M.; Herdtweck, E.; Bach, T. Eur. J. Org. Chem. 2004, 4582-4595.

11. Wu, Y.-J. Name Reactions in Carbocyclic Ring Formations, Li, J. J., Ed., Wiley: Hoboken, NJ, 2010; pp 451-488.

编译自:J.J. Li, Name Reactions: A Collection of Detailed Mechanisms and Synthetic Applications, de Mayo reaction,page 200-201.

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