Reactivity of hydroxyl groups of 1,6 : 2,3- and 1,6 : 3,4-dianhydrido-β-D-hexapyranoses in methylation with iodomethane

Abstract

Relative rate constants for reaction of 1,6 : 2,3- and 1,6 : 3,4-dianhydro-β-D-hexapyranoses with iodomethane in acetonitrile in the presence of silver oxide were measured. Their values, ranging from 1 to 8.6 were interpreted on the basis of polar and steric effects and intramolecular hydrogen bonds.