STUDIES ON REACTIONS RELATING TO CARBOHYDRATES AND POLYSACCHARIDES.: XLV. THE POLYMERIZATION, UNDER THE INFLUENCE OF HEAT, OF CERTAIN COMPOUNDS CONTAINING THE ETHYLENE OXIDE RING

Abstract

The tendency of certain glycidol and glycoloside derivatives to polymerize under the influence of heat has been investigated. Phenyl glycidol, methyl glycidol, and 2:3, 6:7-di-epoxy-4, 5-dihydroxy octane all undergo polymerization. With phenyl glycidol acetate the tendency is much less pronounced, while polymerization does not occur with phenyl glycidol methyl ether. Apparently the phenomenon is associated with the presence of a hydrogen atom capable of migration. Polymerized phenyl glycidol was found to have an open-chain structure containing one ethylene oxide ring. 2-Methoxy ethyl glycoloside was obtained as a stable dimer, which appears to have a dioxane structure.