Abstract
The oxidation of 3- O-methyl- d-glucopyranose (Glc3Me) by Cr VI in acid medium yields Cr III, formic acid and 2- O-methyl- d-arabinose as final products when a 50-times or higher excess of Glc3Me over Cr VI is used. The redox reaction takes place through the combination of Cr VI → Cr IV → Cr II and Cr VI → Cr IV → Cr III pathways. Intermediacy of free radicals and Cr II in the reaction was demonstrated by the observation of induced polymerization of acrylamide and detection of CrO 2 2+ formed by reaction of Cr II with O 2. Intermediate oxo-Cr V–Glc3Me species were detected by EPR spectroscopy. In 0.3–0.5 mol/L HClO 4, intermediate Cr V rapidly decompose to the reaction products, while, at pH 5.5–7.5, where the redox processes are very slow, five-coordinate Cr V bis-chelates of the pyranose and furanose forms of Glc3Me remain more than 15 h in solution. The C1–C2 bond cleavage of Glc3Me upon reaction with Cr VI distinguishes this derivative from glucose, which is oxidized to gluconic acid.
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