cis-and trans-5-Deuteriocyclo-octyl p-bromobenzenesulphonates have been prepared and their kinetic isotope effects and extent of transannular (C-5-→ C-1) hydride shift have been determined for buffered acetolysis. The trans-isomer shows a significant effect (kH/kD= 1.12) and there is a 10:1 preference for trans-5-hydride migration.
W. Parker and C. I. F. Watt, J. Chem. Soc., Perkin Trans. 2, 1975, 1647 DOI: 10.1039/P29750001647
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