THE BEHAVIOR OF L-SORBOSE TOWARDS ANHYDROUS HYDROGEN FLUORIDE

Article abstract of DOI:10.1016/S0008-6215(00)90290-8

L-Sorbose was converted into a mixture of L-sorbose dianhydrides by treatment with anhydrous hydrogen fluoride.Of the six dianhydrides isolated, two were known compounds.The structures have been established by n.m.r. spectroscopy.The relative amounts of dianhydrides obtained depended on the reaction conditions.By use of 13C-n.m.r. spectroscopy, the reaction of L-sorbose with hydrogen fluoride was shown to involve L-sorbofuranosyl fluoride as an intermediate.Dianhydrides were also formed when L-sorbose was treated with methanol and sulfuric acid under Fischer glycosidation condition, or with trifluoroacetic acid.