Sulfuric acid-catalyzed acetolysis of anomeric ethyl 2,3,4,6-tetra-O-acetyl-d-glucopyranosides: kinetics and mechanism

Kinetics of the acetolysis and concomitant anomerization of ethyl 2,3,4,6-tetra-O-acetyl-α- and -β-d-glucopyranosides in a mixture of acetic anhydride, acetic acid, and sulfuric acid have been studied. The progress of the reactions was followed by gas chromatography, and the rate constants of the partial reactions were calculated on the basis of the time-dependent product distributions obtained. The mechanisms of the reactions are discussed.