Oxoammonium salts. 9. Oxidative dimerization of polyfunctional primary alcohols to esters. An interesting β oxygen effect

Article abstract of DOI:10.1021/jo049461j

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 β oxygen. In the absence of a β 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 β-oxygenated compounds. δ Lactones have been prepared from diethylene glycol and 2,2′-thiodiethanol, without sulfur oxidation.