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.
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.
Bock
K
K
Department of Organic Chemistry, Technical University of Denmark, Lyngby.
Pedersen
C
C
Defaye
J
J
Gadelle
A
A
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*
D004187:Disaccharides; D013013:Sorbose; D006858:Hydrofluoric Acid