THE BEHAVIOUR OF D-FRUCTOSE AND INULIN TOWARDS ANHYDROUS HYDROGEN FLUORIDE

Article abstract of DOI:10.1016/0008-6215(85)85185-5

Inulin and D-fructose are quantitatively converted into a mixture of D-fructose dianhydrides on treatment with anhydrous hydrogen fluoride.Of the six dianhydrides isolated, five are known compounds, whereas one, β-D-fructofuranose β-D-fructopyranose 2,1':3,2'-dianhydride, has not been described hitherto.The structures of two of the known dianhydrides have been revised.The relative amounts of dianhydrides obtained depend on the reaction conditions.The reaction of D-fructose with hydrogen fluoride is shown, using 13C-n.m.r. spectroscopy, to involve D-fructofuranosyl fluoride as a probable intermediate.Dianhydrides are also formed when D-fructose is treated with methanol and sulfuric acid under Fischer glycosidation conditions or with trifluoroacetic acid.