The mechanism for the rapid rearrangement of the adamantyl cation (1-yl → 2-yl, or vice versa) in sulfuric acid utilises catalytic adamantane in an intermolecular hydride transfer reaction; a slower rearrangement mechanism involves reversible ring-opening of the adamantly skeleton, and allows incorporation of high levels of deuterium.
D. R. Adams, P. D. Bailey, I. D. Collier, S. A. H. Leah and C. Ridyard, Chem. Commun., 1996, 333 DOI: 10.1039/CC9960000333
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