4-Protoadamantanone (I) is converted into epimeric secondary and tertiary alcohols; 4-exo-protoadamantyl derivatives react rapidly to give 2-adamantyl products while 4-endo-protoadamantyl derivatives react more slowly and tend to undergo a degenerate rearrangement before giving ultimately 2-adamantyl products.
D. Lenoir and P. v. R. Schleyer, J. Chem. Soc. D, 1970, 941 DOI: 10.1039/C29700000941
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