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Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 7, Number 2
February 20, 1986 

Oxidations of Cyclohexanols by N-Bromosuccinimide and Sodium Hypochlorite
Kyoo-hyun Chung*, Seong Jin Kim
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.
111 - 113
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