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Synthesis 1996; 1996(6): 699-701
DOI: 10.1055/s-1996-4281
short paper
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Transition Metal Catalyzed Oxidation; 8: 4-Allyl-Substituted 1,2-Naphthoquinones via Tandem ortho-Phenol Oxygenation and Oxy-Cope Rearrangement

Karsten Krohn* , Sven Bernhard
  • *Universität-GH Paderborn, Fachbereich 13, Chemie und Chemietechnik, Fachgebiet Organische Chemie, Warburger Str. 100, D-33098 Paderborn, Germany, Fax +49(5251)603245; E-mail kk@chemie.uni-paderborn.de
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Publication Date:
31 December 2000 (online)

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4-Allyl-1,2-naphthoquinones 3a-3d are prepared in one operation from 2-allyl-1-naphthols 2a-2d involving tandem zirconium-catalyzed tert-butyl hydroperoxide (TBHP) oxidation and oxy-Cope rearrangement.

ortho-quinones - oxy-Cope rearrangement - domino reaction - zirconium catalysis - tert-butyl hydroperoxide oxygenation