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. 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.
Roquette Frères Society, Lestrem cedex, France.
Mathias
M
Ibert
Patrick
P
Fuertès
Nabyl
N
Merbouh
Christian
C
Feasson
Francis
F
Marsais
D005937:Glucaric Acid / Q000737:chemistry*; D005947:Glucose / Q000737:chemistry*; D010084:Oxidation-Reduction; D010658:Phenylglyoxal / Q000031:analogs & derivatives / Q000737:chemistry; D010880:Piperidines / Q000737:chemistry; D013400:Sugar Acids / Q000138:chemical synthesis*; D014233:Tricarboxylic Acids / Q000138:chemical synthesis*
C528764:2,2,6,6-tetramethyl-1-piperidine; D010880:Piperidines; D013400:Sugar Acids; D014233:Tricarboxylic Acids; D005947:Glucose; D010658:Phenylglyoxal; D005937:Glucaric Acid; C006697:benzil