title: Oxoammonium salts. 9. Oxidative dimerization of polyfunctional primary alcohols to esters. An interesting beta oxygen effect.
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.
authors.affiliation: Department of Chemistry, University of Connecticut, Storrs, CT 06269-3060, USA. james.bobbitt@uconn.edu
authors.forename: Nabyl
authors.initials: N
authors.lastname: Merbouh
authors.forename: James M
authors.initials: JM
authors.lastname: Bobbitt
authors.forename: Christian
authors.initials: C
authors.lastname: Brückner