Kinetics of base-catalyzed degradation of phenyl d-gluco-pyranosides
Document Type
Article
Publication Date
1-1-1979
Abstract
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.
Publication Title
Carbohydrate Research
Recommended Citation
Lai, Y.,
&
Ontto, D.
(1979).
Kinetics of base-catalyzed degradation of phenyl d-gluco-pyranosides.
Carbohydrate Research,
75(C), 51-59.
http://doi.org/10.1016/S0008-6215(00)84626-1
Retrieved from: https://digitalcommons.mtu.edu/michigantech-p/7234