Reaction sequences to 1,2- and 2,4-disubstituted adamantanes each involving a protoadamantane → adamantane rearrangement have been developed. Protoadamantan-4-one has been converted into 1-methyladamantan-2-one, adamantane-1,2-diol. 1,2-dichloroadamantane, and 1,2-dibromoadamantane. Protoadamantene has been converted into 2ax,4ax-dibromoadamantane, 2ax,4eq-dibromoadamantane, and 4ax-bromoadamantan-2ax-ol. Oxymercuration of protoadamantene gave only a trace amount of rearrangement product.
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Cuddy et al. (1971) studied this question.
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