羰基化合物和活泼亚甲基化合物在胺催化下缩合的反应。 反应机理 胺作为碱对活泼亚甲基进行拔氢,得到碳负离子。另一分子的胺再和羰基化合物缩合得到亚胺离子。碳负离子进攻亚胺离子,脱掉胺,水解脱羰,得到产物。
1. Knoevenagel, E. Ber. Dtsch. Chem. Ges. 1898, 31, 2596. Emil Knoevenagel (1865- 1921) was born in Hannover, Germany. He studied at Göttingen under Victor Meyer and Gattermann, receiving a Ph.D. in 1889. He became a full professor at Heidelberg in 1900. When WWI broke out in 1914, Knoevenagel was one of the first to enlist and rose to the rank of staff officer. After the war, he returned to his academic work until his sudden death during an appendectomy. 2. Jones, G. Org. React. 1967, 15, 204. (Review). 3. Van der Baan, J. L.; Bickelhaupt, F. Tetrahedron 1974, 30, 2447. 4. Green, B.; Khaidem, I. S.; Crane, R. I.; Newaz, S. S. Tetrahedron 1976, 31, 2997. 5. Angeletti, E.; Canepa, C.; Martinetti, G.; Venturello, P. J. Chem. Soc., Perkin Trans. 1 1989, 105. 6. Paquette, L. A.; Kern, B. E.; Mendez-Andino, J. Tetrahedron Lett. 1999, 40, 4129. 7. Tietze, L. F.; Zhou, Y. Angew. Chem., Int. Ed. 1999, 38, 2045. 8. Balalaie, S.; Nemati, N. Synth. Commun. 2000, 30, 869. 9. Pearson, A. J.; Mesaros, E. F. Org. Lett. 2002, 4, 2001. 10. Curini, M.; Epifano, F.; Marcotullio, M. C.; Rosati, O.; Tsadjout, A. Synth. Commun. 2002, 32, 355. 11. Kourouli, T.; Kefalas, P.; Ragoussis, N.; Ragoussis, V. J. Org. Chem. 2002, 67, 4615. 12. Wada, S.; Suzuki, H. Tetrahedron Lett. 2003, 44, 399. 13. Hu, Yi; Chen, J.; Le, Z.-G.; Zheng, Q.-G. Synth. Comm. 2005, 35, 739. 编译自:Name Reactions (A Collection of Detailed Reaction Mechanisms), Jie Jack Li, Knoevenagel condensation,page 329-330. |
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