Binuclear iron(III) phthalocyanine(μ-oxodimer)/tetrabutylammonium oxone: A powerful catalytic system for oxidation of hydrocarbons in organic solution

Heather M. Neu, Viktor Zhdankin, Victor N. Nemykin

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33 Scopus citations

Abstract

Binuclear iron(III) phthalocyanine-(μ-oxodimer) complex was tested in catalytic oxygenation reactions of several hydrocarbons using tetrabutylammonium oxone as the oxidant in dichloromethane solution at room temperature. Results of the study demonstrate that this is an extremely powerful catalytic system for oxidative conversion of aromatic hydrocarbons (anthracene, 2-tert- butylanthracene, 2-methylnaphthalene, 9, 10-dihydroanthracene, 1,2,3,4-tetrahydronaphthalene, indane, ethylbenzene, toluene, and benzene) to the respective p-quinones in high yields in 5-30 min. Under these conditions, adamantane is oxidized with 71% conversion after 10 min affording a mixture of 1 -adamantanol, 2-adamantanone, 1-hydroxy-2-adamantanone, and 4-protoadamantanone.

Original languageEnglish (US)
Pages (from-to)6545-6548
Number of pages4
JournalTetrahedron Letters
Volume51
Issue number50
DOIs
StatePublished - Dec 15 2010

Bibliographical note

Funding Information:
This work was supported by a research grant from the National Science Foundation (CHE- 1009038 ) and Petroleum Research Fund, administered by the American Chemical Society (grant PRF- 45510-GB-3 ).

Copyright:
Copyright 2017 Elsevier B.V., All rights reserved.

Keywords

  • -oxodimer
  • Catalytic oxidation
  • Iron phthalocyanine μ
  • Oxygenation
  • Tetrabutylammonium oxone

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