Substitution of both chloro and sulfinyl groups of aryl 1-chlorocyclopropyl sulfoxides in one-pot via cyclopropylmagnesium carbenoids: a synthesis of multi-substituted cyclopropanes
作者:Masanobu Yajima、Ryo Nonaka、Hironori Yamashita、Tsuyoshi Satoh
DOI:10.1016/j.tetlet.2009.06.019
日期:2009.8
The rearrangement of cyclopropylmagnesium carbenoids, which were generated from aryl 1-chlorocyclopropyl sulfoxides with a Grignard reagent, to allenes was found to be suppressed by adding HMPA as an additive. Alkylation of the cyclopropylmagnesium carbenoids with the Grignard reagent gives mainly alkylated cyclopropylmagnesium chloride instead. The cyclopropylmagnesium chloride intermediate can be
发现通过添加HMPA作为
添加剂可以抑制由芳基1-
氯环丙基
亚砜与
格氏试剂生成的环丙基
镁类
胡萝卜素重排至
丙二烯。用
格氏试剂将环丙基
镁类化合物烷基化,主要得到的是烷基化的环
丙基氯化镁。环
丙基氯化镁中间体可以用几种亲电试剂捕集,得到多取代的
环丙烷。该程序提供了一种合成多取代
环丙烷的新方法。