Photochemical Alkylation of Ketene Dithioacetal <i>S</i>,<i>S</i>-Dioxides. An Example of Captodative Olefin Functionalization
作者:Ana Maria González-Cameno、Mariella Mella、Maurizio Fagnoni、Angelo Albini
DOI:10.1021/jo990817e
日期:2000.1.1
ketene dithioacetal S,S-dioxides failed through the tin hydride promoted chain process but was successfully performed through stoichiometric photochemical initiation, either by electron transfer or hydrogen abstraction. In the first case, alkyl radicals were produced from tetralkylstannanes (t-Bu-, i-Pr-, n-Bu-SnR(3)) via radical cation fragmentation, while in the second case these were produced from alkanes
某些烯酮二硫缩醛S,S-二氧化物的自由基烷基化未能通过氢化锡促进的链式过程完成,但通过化学计量的光化学引发成功地进行了,无论是电子转移还是氢提取。在第一种情况下,烷基是通过自由基阳离子裂解从四烷基锡烷(t-Bu-,i-Pr-,n-Bu-SnR(3))产生的,而在第二种情况下,它们是从烷烃(环己烷,金刚烷)产生的)二苯甲酮三联体。当涉及庞大的自由基(t-Bu,金刚烷基)时,加成反应具有完全的非对映选择性。