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Oxidation of styrene by 2,3-dichloro-5,6-dicyano-p-benzoquinone

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Abstract

Styrene is oxidized by 2,3-dichloro-5,6-dicyano-p-benzoquinone (DDQ), affording hydroquinone mono(2-phenylethyl) ether. Kinetic studies (50°C in CHCl3) show that the reaction is faster under N2 than under air and takes placevia intramolecular H-atom transfer within the 1:1 and 1:2 DDQ-styrene charge-transfer complexes. The semiquinone radical intermediate is reoxidized to DDQ by O2 when the latter is present, therefore, the apparent rate of DDQ reduction is lower. Stability constants of the CT-complexes and kinetic parameters for the oxidation are reported.

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Authors and Affiliations

  1. Central Research Institute for Chemistry, Hungarian Academy of Sciences, P. O. Box 17, H-1525, Budapest, Hungary

    T. L. Simándi & L. I. Simándi

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  1. T. L. Simándi
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  2. L. I. Simándi
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Simándi, T.L., Simándi, L.I. Oxidation of styrene by 2,3-dichloro-5,6-dicyano-p-benzoquinone. React Kinet Catal Lett 62, 257–262 (1997). https://doi.org/10.1007/BF02475460

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  • DOI: https://doi.org/10.1007/BF02475460

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