Aromatic Cation Activation of Alcohols: Conversion to Alkyl Chlorides Using Dichlorodiphenylcyclopropene
Aromatic Cation Activation of Alcohols: Conversion to Alkyl Chlorides Using Dichlorodiphenylcyclopropene
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DOI：
10.1021/ja906520p
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发表时间：
2009-10-07
影响因子：
15
通讯作者：
Lambert, Tristan H.
中科院分区：
文献类型：
--
作者：
Kelly, Brendan D.;Lambert, Tristan H.
描述了一种通过形成环丙烯醚来活化醇朝向亲核取代的新范例。用3，3-二氯-1，2-二苯基环丙烯处理后，一系列醇底物迅速转化为相应的烷基氯。1H-1 NMR数据支持环丙烯中间体的中间性，并且该反应被证明主要通过1-苯基乙醇的S（N）2机理进行。共提供了12个基板范围的例子。
A novel paradigm for the activation of alcohols toward nucleophilic displacement via formation of cyclopropenium ethers is described. The conversion of a range of alcohol substrates to the corresponding alkyl chlorides occurs rapidly upon treatment with 3,3-dichloro-1,2-diphenylcyclopropene. H-1 NMR data support the intermediacy of a cyclopropenium intermediate, and the reaction is demonstrated to proceed primarily via the S(N)2 mechanism for 1-phenylethanol. A total of 12 examples of substrate scope are provided.