1 拼音
Wolff-Kishner-huáng míng lóng fǎn yìng
醛類或酮類在鹼性條件下與肼作用,羰基被還原爲亞甲基。原來Wolff-Kishner的方法是將醛或酮與肼和金屬鈉或鉀在高溫(約200 °C)下加熱反應,需要在封管或高壓釜中進行,操作不方便。黃鳴龍改進不用封管而在高沸點溶劑如一縮二乙二醇(二甘醇,b.p.245 °C)中,用氫氧化鈉或氫氧化鉀代替金屬鈉反應。
對鹼敏感的化合物不適合用此法還原,可用Clemmensen還原。
2 反應機理
3 反應實例
4 參考文獻
[1] N. Kishner, J. Russ. Phys. Chem. Soc. 43, 582 (1911); C.A. 6, 347 (1912)
[2] L. Wolff, Ann. 394, 86 (1912)
[3] Huang Minlon J. Amer. Chem. Soc. 68, 2487 (1946)
[4] D. Todd in Organic Reactions IV, 378 (1948)
[5] V. Franzen, Chem. Ztg. 80, 667 (1956)
[6] R. A. Braun and W. A. Mosher, J. Amer. Chem. Soc. 80, 4919 (1958)
[7] D. H. R. Barton, D. A. J. Ives and B. R. T. Thomas, J. Chem. Soc. 1955, 2056
[8] J. H. Weisburger and P. H. Grantham, J. Org. Chem. ,1160 (1956)
[9] V. Georgian, R. Harrisson and N. Gubisch, J. Amer. Chem. Soc. 81, 5834 (1959)
[10] D. J. Cram, M. R. V. Sahyun d G. R. Knox, J. Amer. Chem. Soc. 84, 1734 (1962)
[11] S. Hunig and W. Eckardt, Ber. 95, 2498 (1962)
[12] M. F. Grundon, H. B. Henbest and M. D. Scott , J. Chem. Soc. 1963, 1855
[13] E. Muller, G. Fiedler, H. Huber, B. Narr, H. Suhr and K. Witte, Z. Naturforsch. 18B, S (1963)
[14] H. H. Szmant and C. M. Harmuth, J. Amer. Chem. Soc. 86, 2909 (1964).
參見:Clemmensen還原