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Issue 0, 1971
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Oxidation of anthracene with cerium(IV) ammonium nitrate

Abstract

The oxidation of anthracene with cerium(IV) ammonium nitrate appears to occur through an initial anthracene radical cation which is transformed into a transient anthrol nitrate. Homolysis of the oxygen–nitrogen bond of the anthrol nitrate furnishes the nitrite radical and a mesomeric anthrone radical. While the former attacks the initial ion radical with a concerted mechanism to yield anthrol nitrite, the latter undergoes dimerisation to bianthrone, addition of a nitrate radical to yield 9,10-dihydro-10-oxo-9-anthryl nitrate which subsequently disproportionates to anthraquinone and nitrous acid, and oxidation to the anthrone cation. This is attacked by a nucleophile to yield 10-methoxyanthrone or 10-acetoxyanthrone according to the solvent used.

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Article type: Paper
DOI: 10.1039/J29710002238
Citation: J. Chem. Soc. B, 1971,0, 2238-2241

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    Oxidation of anthracene with cerium(IV) ammonium nitrate

    B. Rindone and C. Scolastico, J. Chem. Soc. B, 1971, 0, 2238
    DOI: 10.1039/J29710002238

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