Tetrahedron p. 5627 - 5636 (1986)
Update date:2022-08-03
Topics:
Barton, Derek H. R.
Finet, Jean-Pierre
Motherwell, William B.
Pichon, Clotilde
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.
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