Identification of a boron-containing intermediate in the boron tribromide mediated aryl propargyl ether cleavage reaction

J Org Chem. 2009 Feb 6;74(3):1385-7. doi: 10.1021/jo802207y.

Abstract

An alternate reaction mechanism for the boron tribromide mediated deprotection of aryl propargyl ethers based on the isolation of a key boron-containing byproduct is proposed. On the basis of the new mechanistic insight, we discovered that HBBr(2) x SMe(2) can also be used for cleaving aryl propargyl ethers.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkenes / chemical synthesis*
  • Alkynes / chemistry*
  • Boron Compounds / chemical synthesis
  • Boron Compounds / chemistry*
  • Bromides / chemistry*
  • Ethers / chemistry*
  • Hydrocarbons, Brominated / chemical synthesis*
  • Vinyl Compounds / chemical synthesis

Substances

  • Alkenes
  • Alkynes
  • Boron Compounds
  • Bromides
  • Ethers
  • Hydrocarbons, Brominated
  • Vinyl Compounds
  • propargyl ether