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Synthesis 1997; 1997(2): 173-175
DOI: 10.1055/s-1997-1171
short paper
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(1,2:5,6)-Anthradiquinones by Oxidation of 2,6-Dihydroxyanthracenes

Stephan Zippel, Peter Boldt*
  • *Institut für Organische Chemie der Technischen Universität Braunschweig, Hagenring 30, D-38092 Braunschweig, Germany, E-mail P.Boldt@tu-bs.de
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Publication Date:
31 December 2000 (online)

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For the synthesis of the ortho-anthraquinones 4-6 and 15 from the corresponding 2,6-dihydroxyanthracenes 1-3 and the 2-hydroxyanthracene 14, respectively, we performed a comparative study of the known reagents used for o-quinone preparation from phenols, namely phenylseleninic anhydride, potassium nitrosodisulfonate and tert-butyl hydroperoxide with the Mimoun complex as catalyst. Only phenylselenic anhydride gave the expected compounds in satisfying yields.

Phenylseleninic anhydride is superior to Fremy's salt or tert-butyl hydroperoxide