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Formation of DPM ethers using O-diphenylmethyl trichloroacetimidate under thermal conditions†
Kyle T. Howard,Brian C. Duffy,Matthew R. Linaburg,John D. Chisholm
Organic & Biomolecular Chemistry Pub Date : 12/16/2015 00:00:00 , 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.

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