Fluoroselenenylation of Acetylenes with Xenon Difluoride-Diorganyl Diselenides and Xenon Difluoride-Phenylseleno(trialkyl)silanes
作者:Helmut Poleschner、Matthias Heydenreich、Karla Spindler、Günter Haufe
DOI:10.1055/s-1994-25635
日期:——
A new, efficient method of fluoroselenenylation of terminal, and open-chain symmetric and unsymmetric disubstituted acetylenes and cycloalkynes, gives vicinal (E)-fluoroalkenyl selenides in moderate to high yields by addition of selenenyl fluoride equivalents. These are formed in situ from xenon difluoride and diaryl, dibenzyl or primary and secondary dialkyl diselenides. Alternatively, the benzeneselenenyl fluoride equivalent is formed by treatment of more reactive phenylselenotrialkylsilanes with xenon difluoride. The regiochemistry of the addition is strongly dependent on the steric effects of substituents bonded to the acetylene.
一种新型高效的氟硒烯化方法能够将末端开链对称和非对称二取代乙炔及环炔通过硒烯基氟等效物加成,以中等至高产率得到邻位(E)-氟代烯基硒化合物。这些硒烯基氟等效物是由氙二氟化合物与二芳基、二苄基或初级和次级二烷基二硒化物在原位反应形成的。此外,也可以通过氙二氟化合物处理更具反应活性的苯硒基三烷基硅烷来形成苯硒基氟等效物。加成的区域选择性强烈依赖于乙炔上连接取代基的立体效应。