title: Formation of DPM ethers using O-diphenylmethyl trichloroacetimidate under thermal conditions.
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.
authors.affiliation: Department of Chemistry, 1-014 Center for Science and Technology, Syracuse University, Syracuse, New York 13244, USA. jdchisho@syr.edu.
authors.forename: Kyle T
authors.initials: KT
authors.lastname: Howard
authors.affiliation: Department of Chemistry, 1-014 Center for Science and Technology, Syracuse University, Syracuse, New York 13244, USA. jdchisho@syr.edu.
authors.forename: Brian C
authors.initials: BC
authors.lastname: Duffy
authors.affiliation: Department of Chemistry, 1-014 Center for Science and Technology, Syracuse University, Syracuse, New York 13244, USA. jdchisho@syr.edu.
authors.forename: Matthew R
authors.initials: MR
authors.lastname: Linaburg
authors.affiliation: Department of Chemistry, 1-014 Center for Science and Technology, Syracuse University, Syracuse, New York 13244, USA. jdchisho@syr.edu.
authors.forename: John D
authors.initials: JD
authors.lastname: Chisholm
mesh_terms: D000081:Acetamides / Q000737:chemistry*; D000143:Acids / Q000737:chemistry; D001559:Benzhydryl Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D001713:Biphenyl Compounds / Q000737:chemistry*; D002384:Catalysis; D004987:Ethers / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013696:Temperature
chemical_list: D000081:Acetamides; D000143:Acids; D001559:Benzhydryl Compounds; D001713:Biphenyl Compounds; D004987:Ethers; C000611471:O-diphenylmethyl trichloroacetimidate