Evidence of benzilic rearrangement during the electrochemical oxidation of d-glucose to d-glucaric acid

During the course of the 2,2,6,6-tetramethyl-1-piperidinyloxy free radical-catalyzed electrochemical oxidation of d-glucose to d-glucaric acid a new side-product was observed. This compound was isolated and identified as a tricarboxylic acid of unique structure, which was named maribersonic acid. It...

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Veröffentlicht in:	Carbohydrate research 2011-03, Vol.346 (4), p.512-518
Hauptverfasser:	Ibert, Mathias, Fuertès, Patrick, Merbouh, Nabyl, Feasson, Christian, Marsais, Francis
Format:	Artikel
Sprache:	eng
Schlagworte:	analytical methods Benzilic rearrangement Chemical Sciences Electrochemical oxidation electrochemistry Glucaric Acid - chemistry glucose Glucose - chemistry Maribersonic acid Organic chemistry oxidation Oxidation-Reduction Phenylglyoxal - analogs & derivatives Phenylglyoxal - chemistry Piperidines - chemistry Sugar Acids - chemical synthesis TEMPO Tricarboxylic acid Tricarboxylic Acids - chemical synthesis
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Beschreibung
Zusammenfassung:	During the course of the 2,2,6,6-tetramethyl-1-piperidinyloxy free radical-catalyzed electrochemical oxidation of d-glucose to d-glucaric acid a new side-product was observed. This compound was isolated and identified as a tricarboxylic acid of unique structure, which was named maribersonic acid. Its structure was proven by different experiments coupled with several analytical methods, and its appearance during the electrochemical oxidation of d-glucose was rationalized through a thorough study.
ISSN:	0008-6215 1873-426X 0008-6215
DOI:	10.1016/j.carres.2010.12.017