Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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Oxidations of Cyclohexanols by N-Bromosuccinimide and Sodium Hypochlorite

  • Published : 1986.04.20
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Abstract

The axial alcohol in trans-3,3,5-trimethylcyclohexanol was oxidized more readily than the equatorial alcohol in cis-3,3,5-trimethylcyclohexanol by NBS in aqueous dioxane. On the contrary, the equatorial alcohol was preferentially oxidized to the axial one by 10% aqueous sodium hypochlorite in the presence of tetrabutylammonium hydrogen sulfate (TBHS). The specificity indicates the presence of two different mechanism. In acidic medium, the cleavage of C-H bond is rate determining step while the reactivity of the alcohol is important in the presence of TBHS. The mechanism in basic medium without TBHS will be discussed.

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