酸催化下利用三苯甲醇对芳环进行三苯甲基化的反应。此反应是Friedel–Crafts反应的特殊情况。与FC反应类似，芳香底物的取代基是给电子基团的跟容易进行反应。最常见的底物是酚类。

反应机理

反应实例

Para-tritylphenol (4). To melted PhOH 1 (0.5 g) in HOAc (5 mL) was added triphenylcarbinol 2 (0.5 g). The mixture was heated, if necessary, to obtain a solution, then cooled and conc H2SO4 (0.90 g) was added. The crystals, formed after prolonged storage, were filtered, washed thoroughly with acetic acid and recrystallised from ethanol to give pure product 4 (93%).

Ortho-tritylphenol (5). Triphenylcarbinol 2 (0.5 g) was added to melted PhOH (1 g). The reaction mixture was heated on steam bath to 100 C. A few drops of conc H2SO4 were added and heating was continued until the intense color had faded and the solid product appeared. The product was triturated with a small amount of MeOH, filtered and washed with MeOH. Recrystallization from EtOH gave 5 (46%).

【Shulgin AT, J Org Chem, 1962, 27, 3868】

相关文献

1 Baeyer A, Villiger V Chem Ber 1902 35 3013

2 Hardy DVN J Chem Soc 1929 1000

3 Shulgin AT J Org Chem 1962 27 3868

4 Kakosa JM J Org Chem 1983 48 3605

5 Galanin NE Russ J Org Chem 2009 45 1024

编译自：Organic Syntheses Based On Name Reactions, 3RdEd, A. Hassner, Page 20.