Chapter 13. Oxidation and Oxygenation of Substituted Arenes with Alkyl Hydroperoxides or Dioxygen/Mediation by Schiff-Base Complexes

  1. Waldemar Adam
  1. Anton Rieker,
  2. Stefan Förster and
  3. Emerich Eichhorn

Published Online: 30 JUN 2005

DOI: 10.1002/3527600396.ch26

Peroxide Chemistry: Mechanistic and Preparative Aspects of Oxygen Transfer

Peroxide Chemistry: Mechanistic and Preparative Aspects of Oxygen Transfer

How to Cite

Rieker, A., Förster, S. and Eichhorn, E. (2000) Oxidation and Oxygenation of Substituted Arenes with Alkyl Hydroperoxides or Dioxygen/Mediation by Schiff-Base Complexes, in Peroxide Chemistry: Mechanistic and Preparative Aspects of Oxygen Transfer (ed W. Adam), Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim, FRG. doi: 10.1002/3527600396.ch26

Editor Information

  1. Institut für Organische Chemie, Universität Würzburg, Am Hubland, D-97074 Würzburg, Germany

Author Information

  1. Institut für Organische Chemie, Universität Tübingen, Auf der Morgenstelle 18, D-72076 Tübingen, Germany

Publication History

  1. Published Online: 30 JUN 2005
  2. Published Print: 11 SEP 2000

ISBN Information

Print ISBN: 9783527271504

Online ISBN: 9783527600397

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Keywords:

  • dioxygen;
  • no electron transfer (NOET);
  • outer-sphere electron transfer (OSET);
  • inner-sphere electron transfer (ISET);
  • indirect oxygenation (INDO);
  • oxygenation;
  • O2 oxygenations;
  • tyrosine derivatives;
  • thiophenols;
  • anilines;
  • melatonin;
  • t-BuOOH

Summary

This chapter contains sections titled:

  • Introduction

  • Mechanistic Aspects

    • Reactions with Dioxygen

      • No Electron Transfer (NOET) Between Substrate and Metal

      • Outer-Sphere Electron Transfer (OSET)

      • Inner-Sphere Electron Transfer (ISET)

    • Indirect Oxygenation (INDO) with t-BuOOH as Oxidant

  • Oxygenation of Phenols and Thiophenols

    • Regioselectivity in O2 Oxygenations

    • Oxygenation of Tyrosine Derivatives

    • Oxygenation of Thiophenols

    • Mechanistic Implications

  • Oxygenation of Anilines

    • Oxygenation of Anilines with Metal Complexes and t-BuOOH (INDO)

    • Oxygenation of Anilines with O2

  • Oxygenation of Melatonin

    • Oxygenation with t-BuOOH

      • Structure determination

    • Oxygenation with O2

      • Structure determination

    • Mechanistic Considerations

    • Conclusions

  • Summary

  • References