Formation of DPM ethers using O-diphenylmethyl trichloroacetimidate under thermal conditions

Org Biomol Chem. 2016 Feb 7;14(5):1623-8. doi: 10.1039/c5ob02455b.

Abstract

Alcohols are effectively converted to their corresponding diphenylmethyl (DPM) ethers by reaction with O-diphenylmethyl trichloroacetimidate in refluxing toluene without the requirement of a catalyst or other additives. A number of acid and base sensitive substrates were protected in excellent yield using this new method without disturbing the pre-existing functionality present in these molecules. This reaction is the first example of the formation of an ether from stoichiometric amounts of a trichloroacetimidate and an alcohol without the addition of a Brønsted or Lewis acid catalyst.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Acetamides / chemistry*
  • Acids / chemistry
  • Benzhydryl Compounds / chemical synthesis*
  • Benzhydryl Compounds / chemistry
  • Biphenyl Compounds / chemistry*
  • Catalysis
  • Ethers / chemical synthesis*
  • Ethers / chemistry
  • Molecular Structure
  • Temperature*

Substances

  • Acetamides
  • Acids
  • Benzhydryl Compounds
  • Biphenyl Compounds
  • Ethers
  • O-diphenylmethyl trichloroacetimidate