The periodate oxidation of sucrose in aqueous N,N-dimethylformamide.
Sucrose has been oxidized with sodium periodate in 0-50% aqueous N,N-dimethylformamide (DMF). In 50% aqueous DMF the reaction is selective for the glucose ring, yielding a dialdehyde. The increased selectivity is not due to conformational factors but is ascribed to the dissociation of water from cyclic periodate ester species which makes the reaction via the acyclic ester on fructose unfavourable.
de Wit
D
D
Delft University of Technology, Laboratory of Organic Chemistry, The Netherlands.
van den Berg
R
R
Johansson
L A
LA
van Rantwijk
F
F
Maat
L
L
Kieboom
A P
AP
D002240:Carbohydrate Sequence; D004126:Dimethylformamide / Q000737:chemistry; D008969:Molecular Sequence Data; D010084:Oxidation-Reduction; D010504:Periodic Acid / Q000737:chemistry; D012996:Solutions / Q000737:chemistry; D013395:Sucrose / Q000737:chemistry*
D012996:Solutions; D010504:Periodic Acid; D013395:Sucrose; D004126:Dimethylformamide; C009288:metaperiodate