Chlorination of adamantane by ferric chloride or antimony pentachloride gave chloroadamantanes having low 1 : 2 isomer ratios, similar to known radical processes and in contrast to polar reactions.
P. Kovacic and J. C. Chang, J. Chem. Soc. D, 1970, 1460 DOI: 10.1039/C29700001460
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