51575-83-8Relevant articles and documents
Aromatic cation activation of alcohols: Conversion to alkyl chlorides using dichlorodiphenylcyclopropene
Kelly, Brendan D.,Lambert, Tristan H.
supporting information; experimental part, p. 13930 - 13931 (2009/12/25)
(Chemical Equation Presented) 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 the SN2 mechanism for 1-phenylethanol. A total of 12 examples of substrate scope are provided.