Bulletin of the Korean Chemical Society

  • 제7권2호
  • /
  • Pages.111-113
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  • 1986
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  • 0253-2964(pISSN)
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  • 1229-5949(eISSN)
대한화학회 (Korean Chemical Society)
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Oxidations of Cyclohexanols by N-Bromosuccinimide and Sodium Hypochlorite

  • 발행 : 1986.04.20
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초록

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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참고문헌

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피인용 문헌

  1. Effect of Micellar Aggregates on the Kinetics of Dextrose Oxidation by N-Bromosuccinimide vol.47, pp.2, 1986, https://doi.org/10.3139/113.110057
  2. Kinetic Treatment of the Reaction of Fructose and N-Bromosuccinimide in Cationic/Anionic/Nonionic Micelles vol.2014, pp.None, 2014, https://doi.org/10.1155/2014/791563
  3. Use of Bromine and Bromo-Organic Compounds in Organic Synthesis vol.116, pp.12, 1986, https://doi.org/10.1021/acs.chemrev.5b00400