Kinetics of base-catalyzed degradation of phenyl d-gluco-pyranosides

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The kinetics of base-catalyzed cleavage of the glycosidic linkage in phenyl α- and β-d-glucopyranoside have been studied at various concentrations of base, and are interpreted in terms of formation of anionic species as reactive intermediates, accompanied by a minor mechanism of bimolecular, nucleophilic substitution. The data indicate that, in < M sodium hydroxide solution, more than 80% of the cleavage reaction proceeds through an intramolecular-displacement process facilitated by the anchimeric assistance of the hydroxyl group at C-6, and C-2, for the α- and β-d-glycoside, respectively. However, the bimolecular substitution reaction becomes increasingly apparent as the alkalinity is raised above 1.5M concentration of base. © 1979.

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Carbohydrate Research