Synthesis of 1,2-dihydro-1-phenylindeno[2,1-b]-phosphole as a potential precursor of a phosphapentalenyl anion
作者:Louis D. Quin、Alan N. Hughes、H.Franklin Lawson、Annette L. Good
DOI:10.1016/s0040-4020(01)88540-9
日期:1983.1
on abstraction of a proton. However, mixtures of products were obtained with various bases, and with t-butyllithium a 1,4-addition reaction occurred to form a compound identified as 3-tert-butyl-1,2,3,8-tetrahydro-1-phenylindeno[2,1-b]phosphole (isolated as the 1-oxide). Indications were obtained that n-butyllithium and lithium dicyclohexylamide also add to the diene unit of I. Another 1,4-addition
3-乙烯基-1H-茚是在麦考马克与苯基二溴化膦的环加成反应中首次用作二烯。加热加合物以重排双键,并且在水解时获得1,2,3,8-四氢-1-苯基茚并[2,1- b ]磷化氢1-氧化物。溴代醇在水中与NBS形成。除去HBr和H 2 O分子,得到1,2-二氢-1-苯基茚并[2,1-b]氧化磷(I)。该膦是通过用HSiCl 3-吡啶进行脱氧而形成的,并具有适当的饱和度,以使质子提取后形成苯并磷杂戊烯基阴离子。但是,获得了具有不同碱和t的产品混合物。-丁基锂发生1,4-加成反应,形成化合物,鉴定为3-叔丁基-1,2,3,8-四氢-1-苯基茚并[2,1- b ]磷化物(分离为1-氧化物)。得到的迹象表明正丁基锂和二环己基氨基锂也加到了I的二烯单元上。当在没有吡啶的情况下尝试进行HSiCl 3脱氧时,另外的1,4-加成(相当于H 2与I一起发生)。本研究的产物用31 P和13 C NMR光谱表征。对31