Stereocontrolled double ring expansion of fused allylidenecyclopropanes. A novel route to hydroazulenes and other fused bicyclic systems
作者:Craig A. Shook、Matthew L. Romberger、Sang Hun Jung、Manchao Xiao、James P. Sherbine、Birong Zhang、Fu Tyan Lin、Theodore Cohen
DOI:10.1021/ja00076a037
日期:1993.11
A variety of 1-(phenylthio)-1-(trimethylsilyl)cyclopropanes, fused to five-, six-, and seven-membered rings have been prepared by several procedures and reductively lithiated by means of aromatic radical anions. The resulting 1-lithio-1-(trimethylsilyl)cyclopropanes have been treated in most cases with α,β-unsaturated aldehydes, followed by potassium tert-butoxide to yield allylidenecyclopropanes.
多种 1-(苯硫基)-1-(三甲基甲硅烷基)环丙烷与五、六和七元环稠合已通过多种方法制备,并通过芳香基阴离子还原锂化。在大多数情况下,所得的 1-锂硫基-1-(三甲基甲硅烷基)环丙烷已用 α,β-不饱和醛处理,然后用叔丁醇钾处理,生成烯丙基环丙烷。后者在密封管或闪蒸真空热解装置中进行热重排后,会发生双环膨胀,生成环戊烯环己烯、-环庚烯(氢化茚)或-环辛烯