Polonovski反应

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叔胺的氮氧化物用活性试剂(如乙酸酐)处理,重排生成N,N-二取代乙酰胺和醛的反应


反应机理


或者也可能是分子内重排:


反应实例



参考文献

1. Polonovski, M.; Polonovski, M. Bull. Soc. Chim. Fr. 1927, 41, 1190–1208.

2. Michelot, R. Bull. Soc. Chim. Fr. 1969, 4377–4385.

3. Lounasmaa, M.; Karvinen, E.; Koskinen, A.; Jokela, R. Tetrahedron 1987, 43, 2135–2146.

4. Tamminen, T.; Jokela, R.; Tirkkonen, B.; Lounasmaa, M. Tetrahedron 1989, 45, 2683–2692.

5. Grierson, D. Org. React. 1990, 39, 85–295. (Review).

6. Morita, H.; Kobayashi, J. J. Org. Chem. 2002, 67, 5378–5381.

7. McCamley, K.; Ripper, J. A.; Singer, R. D.; Scammells, P. J. J. Org. Chem. 2003, 68, 9847–9850.

8. Nakahara, S.; Kubo, A. Heterocycles 2004, 63, 1849–1854.

9. Thavaneswaran, S.; Scammells, P. J. Bioorg. Med. Chem. Lett. 2006, 16, 2868–2871.

10. Volz, H.; Gartner, H. Eur. J. Org. Chem. 2007, 2791–2801.

11. Pacquelet, S.; Blache, Y.; Kimny, T.; Dubois, M.-A. L.; Desbois, N. Synth. Commun. 2013, 43, 1092–1100.


编译Name Reactions (A Collection of Detailed Reaction Mechanisms), Jie Jack Li, Polonovski reaction,page 486-487.

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