貝克-文卡塔拉曼重排反應
貝克－文卡塔拉曼重排反應（Baker-Venkataraman重排）是2-乙醯氧基苯乙酮衍生物在鹼作為催化劑之下生成1,3-二酮的反应。這個反應常用於製造色酮和黃酮类化合物。[1][2][3][4][5][6][7][8]反应名称来源于化学家W. Baker和Krishnaswamy Venkataraman。[9][10]
反應機理
在鹼作為催化劑的情況之下，首先苯乙酮的羰基α-氫原子被去质子化，形成烯醇负离子。接著烯醇负离子以碳端亲核进攻苯酚酯的碳原子，形成環狀的氧负离子。之後氧负把酚氧挤出去，酰基轉移到苯乙酮一端，反应后酸化得二酮产物。
参见
參考文獻
- ^ T. S. Wheeler. Flavone. Organic Syntheses. 1952, 32: 72 [2009-05-27]. （原始内容存档于2013-10-12）. (also in the Collective Volume (1963) 4:478 (PDF) （页面存档备份，存于互联网档案馆）).
- ^ Jain, P. K.; et al.. A Facile Baker-Venkataraman Synthesis of Flavones using Phase Transfer Catalysis. Synthesis. 1982, 1982: 221–222. doi:10.1055/s-1982-29755.
- ^ Kalinin, A. V.;Da Silva, A. J. M.;Lopes, C. C.;Lopes, R. S. C.;Snieckus, V. Directed ortho metalation - cross coupling links. Carbamoyl rendition of the baker-venkataraman rearrangement. Regiospecific route to substituted 4-hydroxycoumarins. Tetrahedron Lett. 9 July 1998, 39 (28): 4995–4998. doi:10.1016/S0040-4039(98)00977-0.
- ^ Kraus, G. A.; Fulton, B. S. Wood, S.H.J.Org.Chem. 1984, 49, 3212
- ^ Reddy, B.P.; Krupadanam, G.L.D.J. Heterocycl. Chem 1996, 33, 1561
- ^ Kalinin, A.V.; Sneckus, V. Tetrahedron Lett. 1998, 39 4999
- ^ Thasana, N.; Ruchirawat, S. Tetrahedron Lett. 2002, 43, 4515
- ^ Santo, C.M.M.;Sliva, A.M.S. Cavaleiro, J. A.S. Eur.J. Org. Chem. 2003, 4575
- ^ Baker, W. Molecular rearrangement of some o-acyloxyacetophenones and the mechanism of the production of 3-acylchromones. J. Chem. Soc. 1933: 1381–1389. doi:10.1039/JR9330001381.
- ^ Mahal, H. S.; Venkataraman, K. Synthetical experiments in the chromone. group. XIV. Action of sodamide on 1-acyloxy-2-acetonaphthones. J. Chem. Soc. 1934: 1767–1769. doi:10.1039/JR9340001767.
外部链接
- Baker-Venkataraman重排反应 （页面存档备份，存于互联网档案馆）于organic-chemistry.org（英文）