S. Punna, Stéphane Meunier, M. Finn
Jul 9, 2004
Citations
1
Influential Citations
39
Citations
Journal
Organic letters
Abstract
Aryl propargyl ethers and esters are cleaved selectively in the presence of aryl methyl ethers and esters by boron tribromide in dichloromethane. Under the same conditions, allyl ethers undergo very rapid Claisen rearrangement, and benzyl ethers are also cleaved more rapidly than propargyl. A mechanism involving intramolecular delivery of bromide to the propargyl terminus is proposed. [reaction: see text]