Journal of the American Chemical Society

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

BD Kelly, TH Lambert

Index: Kelly, Brendan D.; Lambert, Tristan H. Journal of the American Chemical Society, 2009 , vol. 131, # 39 p. 13930 - 13931

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Citation Number: 42

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. 1H NMR data support the intermediacy of a cyclopropenium intermediate, and the reaction is demonstrated to proceed primarily via ...