A Thio-Staudinger Reaction: Thermolysis of a Vinyl Azide in the Presence of t -Butyl Mercaptan
作者:Ronald R. Sauers、Susan D. Van Arnum
DOI:10.1080/713744560
日期:2003.10.1
The thermal decomposition of E-3-azido-3-hexene-2,5-dione ( 1 ) in protic media gave rise to several novel reactions of the azide 1 including adducts derived from keteneimine 11 . Reaction with t-butyl mercaptan yielded two products, keteneimine-derived mercaptan addition product 20 and a sulfenimine 6 . Trapping of a vinyl nitrene intermediate or a thio-Staudinger reaction was considered as a possible
E-3-azido-3-hexene-2,5-dione (1) 在质子介质中的热分解引起了叠氮化物 1 的几个新反应,包括衍生自烯酮亚胺 11 的加合物。与叔丁基硫醇反应产生两种产物,烯酮亚胺衍生的硫醇加成产物 20 和亚磺亚胺 6 。捕获乙烯基氮烯中间体或硫代-施陶丁格反应被认为是形成亚磺亚胺 6 的可能机制。当在甲醇或叔丁胺中进行热分解时,不存在乙烯基氮烯加成产物 3 和 5 表明硫代-施陶丁格反应有效。