THE CHEMISTRY OF PENTAVALENT ORGANOBISMUTH REAGENTS. Part IX. CLEAVAGE REACTIONS OF α-GLYCOLS

Article abstract of DOI:10.1016/S0040-4020(01)88167-9

A catalytic bismuth system (Ph₃Bi-NBS-K₂CO₃-CH₃CN with 1percent water) for the cleavage of α-glycols is shown to have a different mechanism from the cyclic process observed with the stoichiometric Bi reagents previously studied.The catalytic system cleaves cis- and trans-decalin-9,10-diols at nearly the same rate, whereas the stoichiometric system does not cleave the trans-9,10-diol.Evidence for the insertion of triphenylbismuth into a hypobromite bond followed by fragmentation of the thus formed Bi intermediate has been secured.