Abstract
A general mechanism for oxidizing reducing sugars (pentoses, hexoses and disaccharides) by OsO4 in alkaline medium is proposed. The reactions exhibit pseudounimolecular kinetics with respect to OsO4, are first order with respect to lower [sugar] and [OH−], but tend towards zeroth order with respect to both higher [sugar] and [OH−]. These results suggest the formation of an activated complex between the enediol andd osmium tetroxide, which slowly disproportionates to give osmium(VI) species and the intermediate products. The reaction products were identified. When an aldehydo sugar is treated with alkali, structural changes occur and an equilibrium is set up, mainly involving a keto sugar product and the starting aldehydo sugar consumed. This process is reversible. These changes are mainly due to the well-known Lobry-de-Bruyn-Alberda Van Ekenstein transformations.
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