Generation and Trapping of Phosphorus Stabilized 4,5-Ethylenedithio-1,3-dithiol-2-ide Carbanions: Synthesis of Ethylenedithio-1,3-dithiafulvalenes
作者:Adrian J. Moore、Martin R. Bryce
DOI:10.1055/s-1991-26370
日期:——
2-Dimethoxyphosphoryl-5,6-dihydro-1,3-dithiolo[4,5-b][1,4]-2-dithiin (8) and 2-triphenylphosphonio-5,6-dihydro-1,3-dithiolo-[4,5-b][1,4]dithiin tetrafluoroborate (9) have been obtained in four steps from 4,5-ethylenedithio-1,3-dithiole-2-thione (4) (ca. 75% overall yield). Deprotonation of (8) and (9) yields the corresponding carbanion (10) and ylide (11) which have been trapped in good yield with glyoxal, cyclopentanone and anthraquinone to afford ethylenedithio-1,3-dithiafulvalenes.
2-二甲氧基磷酸基-5,6-二氢-1,3-二噻烷-[4,5-b][1,4]-2-二硫烯 (8) 和 2-三苯基磷酸根-5,6-二氢-1,3-二噻烷-[4,5-b][1,4]二硫烯四氟硼酸盐 (9) 通过四个步骤从 4,5-乙烯二硫-1,3-二硫烯-2-硫酮 (4) 获得,整体产率约为 75%。对 (8) 和 (9) 去质子化得到相应的负离子 (10) 和亚磷烯 (11),这两者与乙二醛、环戊酮和蒽醌反应,良好地捕获了产物,生成乙烯二硫-1,3-二硫丰烯。