在低温条件下,芳基化合物和醛在酸催化合成二芳基甲烷的反应。此反应是Friedel–Crafts类型反应,因此此反应底物必须含有给电子基团(吸电子取代基)的芳基化合物才能进行。
反应机理
同Friedel–Crafts反应,亲电取代机理。
反应实例
【Chemische Berichte, 1990, 123, 2207-2226】
Ditolylethane (4). To ice cooled PhMe 1 (557 g, 642 mL) was added simultaneously acetaldehyde 2 (77 g, 1.67 mol) in 420 mL of 1 and 95% H2SO4 (655 g) over 2 h. After stirring for 1 h, water (1000 mL) was added cautiously and the organic layer was wased (5% NaOH, water). Vacuum
distillation gave 101 g of 4 (88%).
【Matsuda K, J Org Chem., 1963, 27, 3256】
【Organic Letters, 2013, 15, 2494-2497】
相关文献
1 Baeyer A Chem Ber 1872 5 280
2 Hein DW J Org Chem 1961 26 2539
3 Schnell W Angew Chem Int 1962 75 622
4 Matsuda K J Org Chem 1963 27 3256
5 Yin Y Tet Lett 2006 47 2291
6 Roy S J Org Chem 2007 72 3129
7 Zhou MM Synlett 2008 1096