Criegee Glycol Oxidation

Abstract

The oxidation of 1,2‐diols (or glycols) to aldehydes or ketones with lead tetraacetate [Pb(OAc) 4 , LTA] via the cleavage of C‐C bond between the hydroxyl‐carrying carbon atoms is generally known as Criegee Glycol oxidation. This reaction has been reported to occur only in anhydrous organic solvent and the oxidation rate depends greatly on the structure of glycol and corresponding solvent. The study finds that the oxidation of cis ‐diol is faster than trans ‐diol on a six‐membered ring for this oxidation. During the oxidation of most of the sugars have been found to get oxidized readily in aqueous solution except sucrose. The oxidation from excess lead tetraacetate gives aldehydes or ketones and carbon dioxide and the decomposition of lead tetraacetate holds an ionic mechanism. This reaction has been applied for the analysis of carbohydrate structures.