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

Kyle T. Howard, Brian C. Duffy, Matthew R. Linaburg, John D. Chisholm

Research output: Contribution to journalArticlepeer-review

15 Scopus citations

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.

Original languageEnglish (US)
Pages (from-to)1623-1628
Number of pages6
JournalOrganic and Biomolecular Chemistry
Volume14
Issue number5
DOIs
StatePublished - Feb 7 2016

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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