Skip to main content
SpringerLink
Log in

An environmentally benign method for oxidation of oximes with potassium permanganate supported on kieselguhr under solvent-free conditions

  • Published:
Research on Chemical Intermediates Aims and scope Submit manuscript

Abstract

A rapid and highly efficient procedure for oxidative cleavage of oximes to their parent aldehydes and ketones by grinding with potassium permanganate supported on kieselguhr at room temperature under solvent-free conditions with yields between 82 and 96 % is described. This method has advantages over previous methods used with potassium permanganate oxidation.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Scheme 1

Similar content being viewed by others

References

  1. T.W. Green, P. Wuts, Protective Groups in Organic Synthesis, 2nd edn. (Wiley, New York, 1991)

    Google Scholar 

  2. P. Laszlo, E. Polla, Synthesis, 439 (1985)

  3. G.W. Kabalka, R.D. Pace, P.P. Wadgaonkaf, Synth Commun 20, 2453 (1990)

    Article  CAS  Google Scholar 

  4. G.S. Zhang, H. Gong, D.H. Yang, M.F. Chen, Synth Commun 29, 1165 (1999)

    Article  CAS  Google Scholar 

  5. S.R. Sandler, W. Karo, Organic Functional Group Preparations, vol. 3, 2nd edn. (Academic Press, San Diego, 1989)

  6. B.C. Ranu, D.C. Sarkar, J Org Chem 53, 878 (1988)

    Article  CAS  Google Scholar 

  7. D.S. Bose, P. Srinivas, Synth Commun 27, 3835 (1997)

    Article  CAS  Google Scholar 

  8. P. Salehi, M.M. Khodaei, M. Goodarzi, Synth Commun 32, 1259 (2002)

    Article  CAS  Google Scholar 

  9. M. Narender, M.S. Reddy, N.S. Krishnaveni, K. Surendra, Y.V.D. Nageswar, K.R. Rao, Synth Commun 36, 1463 (2006)

    Article  CAS  Google Scholar 

  10. G.S. Zhang, D.H. Yang, M.F. Chen, K. Cai, Synth Commun 28, 2221 (1998)

    Article  CAS  Google Scholar 

  11. M.M. Heravi, F. Hydarzadeh, Y. Farhangi, M. Ghassemzadeh, J Chem Res (S), 137 (2004)

  12. N. Jain, A. Kumar, S.M.S. Chauhan, Tetrahedron Lett 46, 2599 (2005)

    Article  CAS  Google Scholar 

  13. E.J. Corey, P.B. Hopkins, S. Kim, S. Yoo, K.P. Nambiar, J.R. Falck, J Am Chem Soc 101, 7131 (1979)

    Article  CAS  Google Scholar 

  14. D.P. Curran, F. Brill, D.M. Rakiewicz, J Org Chem 49, 1654 (1984)

    Article  CAS  Google Scholar 

  15. R. Balicki, L. Kaczmarek, Synth Commun 21, 1777 (1991)

    Article  CAS  Google Scholar 

  16. A. Shaabani, S. Naderi, A. Rahmati, Z. Badri, M. Darvishi, D.G. Lee, Synthesis, 3023 (2005)

  17. R. Hajipour, A.E. Ruoho, J Iran Chem Soc 1, 159 (2004)

    Article  CAS  Google Scholar 

  18. I. Mohammadpoor-Baltork, M.M. Khodaei, A.R. Hajipour, E. Aslani, Monatsh Chem 134, 539 (2003)

    Article  CAS  Google Scholar 

  19. G.H. Imanzadeh, A.R. Hajipour, S.E. Mallakpour, Synth Commun 33, 735 (2003)

    Article  CAS  Google Scholar 

  20. W. Chrisman, M.J. Blankinship, B. Taylor, C.E. Harris, Tetrahedron Lett 42, 4775 (2001)

    Article  CAS  Google Scholar 

  21. V.K. Jadhav, P.P. Wadgaonkar, P.L. Joshi, M.M. Salunkhe, Synth Commun 29, 1989 (1999)

    Article  CAS  Google Scholar 

  22. Y.F. Zhou, F. Lin, X.L. Lu, C. Zhang, Q. Wang, X. Zou, J.D. Lou, Oxid Commun 35, 72 (2012)

    CAS  Google Scholar 

  23. L. Zhu, C. Huang, C. Shi, F. Lin, C. Zhang, J. Lou, Oxid Commun 35, 389 (2012)

    CAS  Google Scholar 

  24. J. Lou, F. Lin, L. Huang, X. Zou, Synth React Inorg Met Org Nano Met Chem 42, 1027 (2012)

    Article  CAS  Google Scholar 

  25. L. Zhu, C. Huang, C. Shi, F. Lin, C. Zhang, J. Lou, Oxid Commun 35, 394 (2012)

    CAS  Google Scholar 

  26. A.J. Fatiadi, Synthesis, 85 (1987)

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

    Google Scholar 

  28. A. Mckillop, D.W. Young, Synthesis, 401 (Part 1) and 481 (Part 2) (1979)

  29. P. Laszlo, Preparative Chemistry Using Supported Reagents (Academic Press, San Diego, 1987)

    Google Scholar 

  30. K. Smith, Solid Supports and Catalysts in Organic Synthesis (Prentice Hall, New York, 1992)

    Google Scholar 

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

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

Download references

Author information

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
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Zhiyuan Lou
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Jianan Lin
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Wenjin Zheng
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Changhe Zhang
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Ji-Dong Lou
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Ji-Dong Lou.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Zhu, LY., Lou, Z., Lin, J. et al. An environmentally benign method for oxidation of oximes with potassium permanganate supported on kieselguhr under solvent-free conditions. Res Chem Intermed 39, 4315–4320 (2013). https://doi.org/10.1007/s11164-012-0948-4

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11164-012-0948-4

Keywords

Search

Navigation