7-exo-Hydroxybicyclo[3.3.1]nonan-3-one (1a) and the 1-methyl homologue (1b) have been synthesised and found to undergo a rapid base-induced intramolecular 3,7-hydride shift. In the case of (1a), the associated activation energy (ΔG‡ 19.4 ± 0.2 kcal mol–1 at 113 °C) has been determined by variable temperature 1H n.m.r. spectroscopy.
R. S. Henry, F. G. Riddell, W. Parker and C. I. F. Watt, J. Chem. Soc., Perkin Trans. 2, 1976, 1549 DOI: 10.1039/P29760001549
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