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A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species
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Oxoammonium salts. 9. Oxidative dimerization of polyfunctional primary alcohols to esters. An interesting beta oxygen
Nabyl Merbouh1, James M Bobbitt, Christian Brückner
1Department of Chemistry, University of Connecticut, Storrs, CT 06269-3060, USA. james.bobbitt@uconn.edu
Abstract:
The use of the oxidant 4-acetylamino-2,2,6,6-tetramethylpiperidine-1-oxoammonium tetrafluoroborate in combination with pyridine for the oxidative, dimeric esterification of primary alcohols is described. The ester is the predominant product of the reaction with alcohols containing a beta oxygen. In the absence of a beta oxygen, the corresponding aldehyde is found in appreciable amounts, but a concentration effect can be observed. In the absence of pyridine, little ester is formed, and no appreciable reaction takes place with beta-oxygenated compounds. Delta lactones have been prepared from diethylene glycol and 2,2'-thiodiethanol, without sulfur oxidation.
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