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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.

SUBMITTER: Howard KT

PROVIDER: S-EPMC4986612 | biostudies-literature | 2016 Feb

REPOSITORIES: biostudies-literature

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

Howard Kyle T KT Duffy Brian C BC Linaburg Matthew R MR Chisholm John D JD

Organic & biomolecular chemistry 20160201 5

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 tr ...[more]

PMID: 26691695

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