The mechanism of the hydrolysis of glycofuranosides

Journal of the Chemical Society B: Physical Organic Pub Date: DOI: 10.1039/J29670000185

Abstract

The mechanism of the acid-catalysed hydrolysis of a series of aldofuranosides has been investigated. These reactions are shown to involve glycosyl–oxygen fission and an initial rapid proton-transfer. The entropies of activation, which are all negative, are interpreted in terms of either a bimolecular displacement of MeOH or EtOH by H2O, or a mechanism involving ring-opening.

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