The relative base-catalysed incorporation of deuterium into exo- and endo-6-hydroxybicyclo[3,3,1]-nonan-2-one points to an intramolecular transannular 6,2-hydride shift occurring stereospecifically in the exo-isomer.
W. Parker and J. R. Stevenson, J. Chem. Soc. D, 1969, 1289 DOI: 10.1039/C29690001289
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