Feldman Ken S., Mareska David. A.
Chemistry Department, The Pennsylvania State University, University Park, Pennsylvania 16802.
J Org Chem. 1999 Jul 23;64(15):5650-5660. doi: 10.1021/jo9907538.
The addition of simple pentadienyltosylamide derivatives to the two-carbon electrophile phenyl(propynyl)iodonium triflate initiates a sequence of transformations that furnishes complex, highly functionalized cyclopentenannelated dihydropyrrole products in moderate yields with complete stereoselection. This sequence demonstrates that diyls resulting from homolytic scission of alkylidene carbene-alkene adducts can be readily accessed under mild experimental conditions and that, in the presence of appropriate pendant functionality, these diyls can productively cyclize. The isomeric isoprene-derived tosylamides follow an abbreviated reaction course and deliver azabicyclo[3.1.0]hexanes via an isomerization that competes with diyl formation.
向双碳亲电试剂三氟甲磺酸苯基（丙炔基）碘鎓盐中添加简单的戊二烯基对甲苯磺酰胺衍生物，引发了一系列转化反应，以中等产率和完全的立体选择性得到复杂的、高度官能化的环戊烯并环二氢吡咯产物。该反应序列表明，在温和的实验条件下可以很容易地获得由亚烷基卡宾-烯烃加合物均裂产生的二自由基，并且在存在适当的侧链官能团的情况下，这些二自由基可以有效地环化。异构的异戊二烯衍生的对甲苯磺酰胺遵循简化的反应过程，并通过与二自由基形成竞争的异构化反应生成氮杂双环[3.1.0]己烷。
