Thio-sugars. Part V. Rates of the nucleophilic substitution reactions of some 1,2:5,6-di-O-isopropylidene-3-O-tosyl-α-D-hexoses with potassium thiobenzoate

Abstract

The rates of these reactions in dimethylformamide, monitored by ¹H n.m.r. spectroscopy, have been measured for derivatives of gulose, allose, glucose, and galactose, and found to decrease in that order. From the reactions with the derivatives of gulose, allose, and glucose, 3-S-benzoyl-1,2:5,6-di-O-isopropylidene-3-thio-α-D-galactose, -glucose, and -allose, respectively, were isolated, and their ¹H n.m.r. spectra are recorded.