Abstract:Evidence is presented to show that in the acetolysis of isotopically labeled exo- or endo-2-norbornyl brosylate (exo- or endo-1-OBs) in NaOAc buffered HOAc, the initially formed product, exo-1-OAc, could undergo further isotopic scrambling during its subsequent contact with the reaction medium. These scramblings in the acetate apparently involved relatively large amounts of rearrangement of the label from C-2 to -3. After partial acetolysis of exo- or endo-1-OBs-2-d, n.m.r. analysis showed that the recovered e… Show more
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