Summary
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1.
As a result of the hydrogenation of the quinone (I) over Raney nickel there was formed a previously undescribed readily oxidizable hydroquinone (III), which was characterized as the quinhydrone, the diacetic ester, and the bis(phenylurethan).
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2.
In the condensation of anthracene with 1,4-naphthoquinone in acetic anhydride, the formation of the diacetate (IV) is accompanied by oxidation of the hydroquinone (III) to the quinone (I) by unchanged 1,4-naphthoquinone. Under the conditions of the reaction the latter gives 1,4-naphthalenediol diacetate.
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Literature cited
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Balandin, A.A., Klabunovskii, E.I. & Antik, L.V. Synthesis and transformation of (dimydroanthrylene) naphthohydroquinone (contribution to the stereochemistry of catalysis). Russ Chem Bull 10, 2046–2048 (1961). https://doi.org/10.1007/BF01182952
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DOI: https://doi.org/10.1007/BF01182952