CHEMISTRY OF OXO-SUGARS (1). REARRANGEMENT OF 2-OXOGLYCOSIDES IN PYRIDINE : EVIDENCE OF INTRAMOLECULAR HYDRIDE SHIFT

Methyl α- and β-D-arabinohexopyranosid-2-uloses rearranged, in pyridine, into methyl α- and β-D-ribo-hexopyranosid-3-uloses through intermediacy of methyl α- and β-D-arabinohexopyranosid-3-uloses, respectively, indicating that an intramolecular hydride shift is the initial reaction for rearrangement of 2-oxoglycosides.