THE REACTION OF DIOXANE WITH HYDROGEN BROMIDE

Abstract

Dioxane reacted slowly at room temperature with anhydrous, bromine free hydrogen bromide to form 2, 2′-dibromodiethyl ether as a principal product. The 2, 2′-dibromodiethyl ether was characterized by comparison with a known sample, analysis, molecular weight determination, and by conversion to divinyl ether which was subsequently brominated to yield 1, 1′, 2, 2′-tetrabromodiethyl ether. When refluxed with constant boiling hydrobromic acid 2, 2′-dibromodiethyl ether was partially converted to ethylene dibromide. An intermediate compound in the formation of 2, 2′-dibromodiethyl ether from dioxane and hydrogen bromide was isolated by solvent extraction using petroleum ether. Its properties indicated that it was probably an oxonium salt.