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The energetics of a readily occurring intramolecular hydride shift

Journal of the Chemical Society Perkin Transactions 21976Iss. 13, pp. 1549–1549

Rodney S. Henry, Frank G. Riddell, W. Parker, C. Ian F. Watt

Abstract

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.

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