Secondary β-deuterium isotope effects measured for acetolysis of exo-9-deuterio-exo-8-deltacyclyl brosylate (VI) and exo-9-deuterio-endo-8-deltacyclyl brosylate (VIII) support the direct generation of a delocalized intermediate (III) from exo-brosylate (I-OBs) and a localized ion (IV) from endo-brosylate (II-OBs).
P. K. Freeman and J. N. Blazevich, J. Chem. Soc. D, 1969, 1357b DOI: 10.1039/C2969001357B
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