Acetolysis of 2,4-dinitrophenyl glycopyranosides

Abstract

A linear free energy relationship exists between rates of acetolysis of 2,4-dinitrophenyl glycopyranosides and rates of acid-catalysed hydrolysis of the methyl glycosides. For the 2-acetamido-2-deoxy-β-D-glucopyranosyl glycone, however, amide group participation is more important in acetic acid. Products from the other glycones are 1-O-acetylglycopyranoses, 60 ± 3% inverted. The α-deuterium kinetic isotope effect k_H/k_D for the acetolysis of 2,4-dinitrophenyl β-D-galactopyranoside is 1.099 ± 0.016.