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. 2009 Oct 7;131(39):13930-1.
doi: 10.1021/ja906520p.

Aromatic cation activation of alcohols: conversion to alkyl chlorides using dichlorodiphenylcyclopropene

Brendan D Kelly  1 , Tristan H Lambert
Affiliations

Aromatic cation activation of alcohols: conversion to alkyl chlorides using dichlorodiphenylcyclopropene

Brendan D Kelly et al. J Am Chem Soc. .

Abstract

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. (1)H 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.

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