Cyclohexane, methylcyclohexane, and adamantane are hydroxylated by a radical process using perbenzoic acid. A regioselectivity of 60–90% in favour of tertiary alcohols is noted. In the case of cis and trans decalins, stereoselection leading to 9-decalols can reach 97%. Such a stereoselectivity for hydroxylation by use of a peracid does not necessarily indicate lack of a radical pathway.
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Fossey et al. (1985) studied this question.