title: Steric and electronic effects in the formation of dihexulose dianhydrides. Reaction of racemic sorbose in anhydrous hydrogen fluoride and a facile synthesis of D-sorbose.
abstract: Treatment of DL-sorbose with anhydrous hydrogen fluoride gave a high yield of alpha-D-sorbopyranose alpha-L-sorbopyranose 1,2':2,1'-dianhydride. Similarly a mixture of D-fructose and D-sorbose gave a good yield of beta-D-fructopyranose alpha-D-sorbopyranose 1,2':2,1'-dianhydride. The formation of these products compared to the more complicated mixtures of compounds obtained by treatment of L-sorbose or D-fructose with hydrogen fluoride, is discussed in terms of conformations, and steric and electronic factors.
authors.affiliation: Department of Organic Chemistry, Technical University of Denmark, Lyngby.
authors.forename: K
authors.initials: K
authors.lastname: Bock
authors.forename: C
authors.initials: C
authors.lastname: Pedersen
authors.forename: J
authors.initials: J
authors.lastname: Defaye
authors.forename: A
authors.initials: A
authors.lastname: Gadelle
mesh_terms: D002236:Carbohydrate Conformation; D002240:Carbohydrate Sequence; D004187:Disaccharides / Q000138:chemical synthesis* / Q000737:chemistry; D004563:Electrochemistry; D006858:Hydrofluoric Acid; D009682:Magnetic Resonance Spectroscopy; D008969:Molecular Sequence Data; D015394:Molecular Structure; D013013:Sorbose / Q000138:chemical synthesis / Q000737:chemistry*
chemical_list: D004187:Disaccharides; D013013:Sorbose; D006858:Hydrofluoric Acid