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An efficient and selective oxidation of benzylic and aromatic allylic alcohols with manganese dioxide supported on kieselguhr under solvent-free conditions

Research on Chemical Intermediates volume 39, pages 4287–4292 (2013)Cite this article

Abstract

An efficient and selective oxidation of benzylic and aromatic allylic alcohols to the corresponding aldehydes and ketones with manganese dioxide supported on kieselguhr at 50–55 °C under solvent-free conditions in yields between 82 and 96 % is described. All the reactions are completed within 4 h. The merits of the present procedure by comparing with those reporting manganese dioxide oxidation are listed and the possible oxidation mechanism is also described. Aliphatic primary alcohols remain intact by this method.

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Scheme 1
Scheme 2

References

  1. T.W.G. Solomons, C.B. Fryhle, Organic Chemistry, 8th edn. (Wiley, New York, 2004)

    Google Scholar 

  2. M.B. Smith, J. March, March’s Advanced Organic Chemistry: Reactions, Mechanisms, and Structure, 6th edn. (Wiley, New York, 2007)

    Google Scholar 

  3. A.H. Haines, Methods for the Oxidation of Organic Compounds, Alcohols, Alcohol Derivatives, Alkyl Halides, Nitroalkanes, Alkyl Azides, Carbonyl Compounds, Hydroxyarenes and Aminoarenes (Academic, London, 1988)

    Google Scholar 

  4. L. Fieser, F.M. Fieser, Reagents for Organic Synthesis, vol. 1 (Wiley, New York, 1967). and subsequent volumes in the series

    Google Scholar 

  5. F. Freeman, in Organic Synthesis by Oxidation with Metal Compounds, ed. by W.J. Mijs, C.R.H.I. de Jonge (Plenum, New York, 1986)

    Google Scholar 

  6. S.V. Ley, A. Madin, in Comprehensive Organic Synthesis, vol. 7, ed. by B.M. Trost, I. Fleming (Pergamon, London, 1991)

    Google Scholar 

  7. G. Cainelli, G. Cardillo, Chromium Oxidations in Organic Chemistry (Springer, Berlin, 1984)

    Book  Google Scholar 

  8. A. J. Fatiadi, Synthesis 65(Part 1) and 133(Part 2) (1976)

  9. R.J. Highet, W.C. Wildman, J. Am. Chem. Soc. 77, 4399 (1955)

    Article  CAS  Google Scholar 

  10. R.J. Gritter, T.J. Wallace, J. Org. Chem. 24, 1051 (1959)

    Article  CAS  Google Scholar 

  11. E.F. Pratt, J.F. Van de Castle, J. Org. Chem. 26, 2973 (1961)

    Article  CAS  Google Scholar 

  12. H. Firouzabadi, B. Karimi, M. Abbassi, J. Chem. Res. (S), 236 (1999)

  13. J.D. Lou, Z.N. Xu, Tetrahedron Lett 43, 6149 (2002)

    Article  CAS  Google Scholar 

  14. R.S. Varma, R.K. Saini, R. Dahiya, Tetrahedron Lett 38, 7823 (1997)

    Article  CAS  Google Scholar 

  15. B.M. Khadilkar, S.A. Gadre, V.D. Makwana, V.R. Madyar, Indian J. Chem. 37A, 189 (1998)

    CAS  Google Scholar 

  16. J.D. Lou, J. Ge, X.N. Zou, C. Zhang, Q. Wang, Y.C. Ma, Oxid. Commun. 34, 361 (2011)

    CAS  Google Scholar 

  17. J.D. Lou, X. Lu, L. Huang, Q. Wang, X. Zou, Synth. React. Inorg. Metal. Org. Nano-Metal. Chem. 41, 1342 (2011)

    Article  CAS  Google Scholar 

  18. L.H. Huang, Y.C. Ma, C. Zhang, Q. Wang, X. Zou, J.D. Lou, Synth. Commun. 42, 3377 (2012)

    Article  CAS  Google Scholar 

  19. L. Huang, Q. Wang, Y. Ma, J.D. Lou, C. Zhang, Synth. Commun. 41, 1682 (2011)

    Article  CAS  Google Scholar 

  20. W. Zheng, C. Huang, C. Zhang, Y. F. Zhou, J. D. Lou, Res. Chem. Intermed. (2012). doi:10.1007/s11164-012-0573-2

  21. J.D. Metzger, Angew. Chem. Int. Ed. 37, 2975 (1998)

    Article  CAS  Google Scholar 

  22. K. Tanaka, F. Toda, Chem. Rev. 100, 1025 (2000)

    Article  CAS  Google Scholar 

  23. F. Sineriz, C. Thomassigny, J.D. Lou, Curr. Org. Synth. 1, 137 (2004)

    Article  CAS  Google Scholar 

  24. I.M. Goldman, J. Org. Chem. 34, 3289 (1969)

    Article  CAS  Google Scholar 

Download references

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Authors and Affiliations

  1. College of Life Sciences, China Jiliang University, Hangzhou, 310018, Zhejiang, China

    Li-Yun Zhu, Jianan Lin, Wenjin Zheng & Ji-Dong Lou

  2. Department of Nutrition & Food Science, University of Maryland, College Park, MD, 20742, USA

    Zhiyuan Lou

  3. Centre for the Research and Technology of Agro-Environmental and Biological Sciences (CITAB)/Department of Biology and Environment, Universidade de Trás-os-Montes e Alto Douro (UTAD), Apartado 1013, 5001-801, Vila Real, Portugal

    Changhe Zhang

  4. Sirnaomics, Inc, 401 Professional Drive, Gaithersburg, MD, 20879, USA

    Ji-Dong Lou

Authors
  1. Li-Yun Zhu
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  2. Zhiyuan Lou
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  3. Jianan Lin
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  4. Wenjin Zheng
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  5. Changhe Zhang
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  6. Ji-Dong Lou
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Correspondence to Ji-Dong Lou.

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Zhu, LY., Lou, Z., Lin, J. et al. An efficient and selective oxidation of benzylic and aromatic allylic alcohols with manganese dioxide supported on kieselguhr under solvent-free conditions. Res Chem Intermed 39, 4287–4292 (2013). https://doi.org/10.1007/s11164-012-0945-7

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  • DOI: https://doi.org/10.1007/s11164-012-0945-7

Keywords

  • Alcohols
  • Kieselguhr
  • Manganese dioxide
  • Oxidation
  • Solvent-free