Metal-Catalyzed Organic Photoreactions. Iron (III)-Catalyzed Photoreactions of Aldo- and Ketohexoses

Article abstract of DOI:10.1246/bcsj.61.513

Under UV irradiation in the presence of iron(III) chloride or iron (III) triflate in pyridine, D-glucose, D-mannose, and D-galactose underwent a selective bond cleavage at the C1-C2 position, producing 4-O-formyl-D-arabinopyranose and 4-O-formyl-D-lyxopyranose.D-Fructose, under the same conditions, gave arabino-γ-lactone.The reaction was interpreted in terms of the photoinduced electron transfer within a chelate of iron ion with the carbohydrate molecule.