2-甲基吡啶氮氧化物用三氟乙酸酐或乙酸酐處理得到2-羥甲基吡啶的反應(yīng), 稱(chēng)為Boekelheide反應(yīng)。吡啶4-位取代的烷基也可以得到相應(yīng)的產(chǎn)物。除了利用酸酐，三氯氧磷作為溶劑回流，則可以得到相應(yīng)的氯代物。利用三氯氧磷進(jìn)行反應(yīng)時(shí)，常常得到吡啶2-位氯代產(chǎn)物?！尽?/p>

反應(yīng)機(jī)理

反應(yīng)實(shí)例

參考文獻(xiàn)

1. Boekelheide, V.; Linn, W. J. J. Am. Chem. Soc. 1954, 76, 1286-1291. Virgil Boekelheide (1919-2003) was a professor at the University of Oregon.

2. Boekelheide, V.; Harrington, D. L. Chem. Ind. 1955, 1423-1424.

3. Katritzky, A. R.; Lagowski, J. M. Chemistry of the Heterocylic N-Oxides, Academic Press: NY, 1971. (Review).

4. Newkome, G. R.; Theriot, K. J.; Gupta, V. K.; Fronczek, F. R.; Baker, G. R. J. Org. Chem. 1989, 54, 1766-1769.

5. Katritzky, A. R.; Lam, J. N. Heterocycles 1992, 33, 1011-1049. (Review).

6. Fontenas, C.; Bejan, E.; Haddou, H. A.; Balavoine, G. G. A. Synth. Commun. 1995, 25, 629-633.

7. Galatsis, P. Boekelheide Reaction. In Name Reactions in Heterocyclic Chemistry; Li,J. J., Ed.; Wiley: Hoboken, NJ, 2005, pp 340-349. (Review).

8. Havas, F.; Danel, M.; Galaup, C.; Tisnès, P.; Picard, C. Tetrahedron Lett. 2007, 48, 999-1002.

9. Dai, L.; Fan, D.; Wang, X.; Chen, Y. Synth. Commun. 2008, 38, 576-582.

10. Das, S. K.; Frey, J. Tetrahedron Lett. 2012, 53, 3869-3872.

編譯自：J.J. Li, Name Reactions: A Collection of Detailed Mechanisms and Synthetic Applications, Boekelheide reaction，page 62-63.

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