Houben-Hoesch反应

  • A+

酚或酚醚和腈类化合物在酸催化下进行酰基化的反应

反应机理

腈先与酸进行络合,然后对苯环进行亲电取代,得到亚胺,水解得到酮。



反应实例

分子内的Houben-Hoesch反应



参考文献

1. Hoesch, K. Ber. Dtsch. Chem. Ges. 1915, 48, 1122. Kurt Hoesch (1882-1932) was born in Krezau, Germany. He studied at Berlin under Emil Fischer. During WWI, Hoesch was Professor of Chemistry at the University of Istanbul, Turkey. After the war he gave up his scientific activities to devote himself to the management of a family business.(去家族企业当经理去了,呵呵)

2. Houben, J. Ber. Dtsch. Chem. Ges. 1926, 59, 2878.

3. Amer, M. I.; Booth, B. L.; Noori, G. F. M.; Proenca, M. F. J. R. P. J. Chem. Soc.,

Perkin Trans. 1 1983, 1075.

4. Yato, M.; Ohwada, T.; Shudo, K. J. Am. Chem. Soc. 1991, 113, 691.

5. Rao, A. V. R.; Gaitonde, A. S.; Prakash, K. R. C.; Rao, S. P. Tetrahedron Lett. 1994,

35, 6347.

6. Sato, Y.; Yato, M.; Ohwada, T.; Saito, S.; Shudo, K. J. Am. Chem. Soc. 1995, 117,

3037.

7. Kawecki, R.; Mazurek, A. P.; Kozerski, L.; Maurin, J. K. Synthesis 1999, 751.

8. Udwary, D. W.; Casillas, L. K.; Townsend, C. A. J. Am. Chem. Soc. 2002, 124, 5294.

9. Sanchez-Viesca, F.; Gomez, M. R.; Berros, M. Org. Prep. Proc. Int. 2004, 36, 135.


编译自:Name Reactions (A Collection of Detailed Reaction Mechanisms), Jie Jack Li, Houben-Hoesch reactionpage 308-309.

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