Transannular brominolysis of 5,7,12,14-tetrahydrodibenzo [c,h][1,6] dithiecins by pyridinium hydrobromide perbromide
作者:Mei-Kuen Au、Thomas C. W. Mak、Tze-Lock Chan
DOI:10.1039/p19790001475
日期:——
A facile ring-opening reaction has been observed for 5,7,12,14-tetra hydrodibenzo[c,h][1,6]dithiecin (5) and 1,4,8,11-tetramethyl-5,7,12,14-tetrahydrodibenzo[c,h][1,6]dithiecin (6) on treatment with pyridinium hydrobromide perbromide. Compound (5) gave mainly bis(o-bromomethylbenzyl) disulphide (9) together with trace amounts of 1,2-bis(bromomethyl)benzene and 1,4-dihydro-2,3-benzodithiin (8). Similar
5,7,12,14-四氢二苯并[ c,h ] [1,6]二硫霉素(5)和1,4,8,11-四甲基-5,7,12的开环反应很容易,14-四氢二苯并[ c,h ] [1,6]二硫霉素(6)在氢溴酸吡啶鎓过溴化物的处理中。化合物(5)主要得到双(邻-溴甲基苄基)二硫化物(9)以及痕量的1,2-双(溴甲基)苯和1,4-二氢-2,3-苯并二硫辛(8)。分离出化合物(6)的类似产物。提出了涉及两个跨环硫原子在这些系统中参与的反应途径。