Skip to main content
SpringerLink
Log in

Oxidation of Iodo- and Bromo-Substituted Polymethylbenzenes in the System PbO2–CF3COOH–CH2Cl2

  • Published:
Russian Journal of Organic Chemistry Aims and scope Submit manuscript

Abstract

The oxidation of mono- and diiodo- and -bromo-substituted polymethylbenzenes (mesitylene and durene) in the system PbO2–CF3COOH–CH2Cl2 at room temperature (2–70 h) leads mainly to the formation of iodo- and bromobenzyl alcohols as result of oxidation of methyl group. The reaction involves intermediate formation of haloarene radical cations. ESR study of these radical cations made it possible to determine the structure of their singly occupied molecular orbitals a2 or b1 and interpret their reactivity.

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

Similar content being viewed by others

References

  1. Miyaura, N., Cross-Coupling Reactions. A Practical Guide, Berlin: Springer, 2002.

    Book  Google Scholar 

  2. Nichihara, Y., Applied Cross-Coupling Reactions, Berlin: Springer, 2013.

    Book  Google Scholar 

  3. Metal-Catalyzed Cross-Coupling Reactions, De Meijere, A. and Diederich, F., Eds., Weinheim: Wiley-VCH, 2004, 2nd ed.

  4. Diederich, F. and Stang, P.J., Metal-Catalyzed Cross-Coupling Reactions, Weinheim: Wiley-VCH, 1998.

    Book  Google Scholar 

  5. Chinchilla, R. and Nájera, C., Modern Alkyne Chemistry: Catalytic and Atom-Economic Transformations, Trost, B.M. and Li, C.-J., Eds., Weinheim: Wiley-VCH, 2014.

  6. Handbook of Organopalladium Chemistry for Organic Synthesis, Negichi, E. and de Meijere, A., Eds., New York: Wiley, 2002.

  7. Seechurn, C.C.C., Kitching, M.O., Colacot, T.J., and Snieckuc, V., Angew. Chem., Int. Ed., 2012, vol. 51, p. 5062.

    Article  CAS  Google Scholar 

  8. Nicolaou, K.C., Bulger, P.G., and Sarlah, D., Angew. Chem., Int. Ed., 2005, vol. 44, p. 4442.

    Article  CAS  Google Scholar 

  9. Chinchilla, R. and Nájera, C., Chem. Rev., 2007, vol. 107, p.874.

    Article  CAS  PubMed  Google Scholar 

  10. Colacot, T.J., Platinum Met. Rev., 2011, vol. 55, p.84.

    Article  Google Scholar 

  11. Gini, A., Brandhofer, T., and Mancheño, O.G., Org. Biomol. Chem., 2017, vol. 15, p. 1294.

    Article  CAS  PubMed  Google Scholar 

  12. Lücke, B., Narayana, K.V., Martin, A., and Jähnisch, K., Adv. Synth. Catal., 2004, vol. 346, p. 1407.

    Article  CAS  Google Scholar 

  13. Combe, S.H., Hosseini, A., Parra, A., and Schreiner, P.R., J. Org. Chem., 2017, vol. 82, p. 2407.

    Article  CAS  PubMed  Google Scholar 

  14. Liu, W. and Groves, J.T., Acc. Chem. Res., 2015, vol. 48, p. 1727.

    Article  CAS  PubMed  Google Scholar 

  15. Aborways, M.M. and Moran, W.J., Tetrahedron Lett., 2016, vol. 57, p.983.

    Article  CAS  Google Scholar 

  16. De Almeida, L.S., Esteves, P.M., and de Mattos, M.C.S., Tetrahedron Lett., 2015, vol. 56, p. 6843.

    Article  CAS  Google Scholar 

  17. Kim, Y.J., Jeong, M.J., Kim, J.E., In, I., and Park, C.P., Aust. J. Chem., 2015, vol. 68, p. 1653.

    Article  CAS  Google Scholar 

  18. Bloom, S., Pitts, C.R., Woltornist, R., Griswold, A., Holl, M.G., and Lectka, T., Org. Lett., 2013, vol. 15, p. 1722.

    Article  CAS  PubMed  Google Scholar 

  19. Neufeld, K., Marienhagen, J., Schwaneberg, U., and Pietruszka, J., Green Chem., 2013, vol. 15, p. 2408.

    Article  CAS  Google Scholar 

  20. Gaster, E., Kozuch, S., and Pappo, D., Angew. Chem., Int. Ed., 2017, vol. 56, p. 5912.

    Article  CAS  Google Scholar 

  21. Rezaeifard, A., Khoshyan, A., Jafarpour, M., and Pourtahmasb, M., RSC Adv., 2017, vol. 7, p. 15754.

    Article  CAS  Google Scholar 

  22. Sterckx, H., De Houwer, J., Mensch, C., Herrebout, W., Tehrani, K.A., and Maes, B.U.W., Beilstein J. Org. Chem., 2016, vol. 12, p.144.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  23. Tripathi, S., Singh, S.N., and Yadav, L.D.S., RSC Adv., 2016, vol. 6, p. 14547.

    Article  CAS  Google Scholar 

  24. Sarma, B.B., Efremenko, I., and Neumann, R., J. Am. Chem. Soc., 2015, vol. 137, p. 5916.

    Article  CAS  PubMed  Google Scholar 

  25. Liu, X., Lin, L., Ye, X., Tan, C.-H., and Jiang, Z., Asian J. Org. Chem., 2017, vol. 6, p.422.

    Article  CAS  Google Scholar 

  26. Tan, J., Zheng, T., Yu, Y., and Xu, K., RSC Adv., 2017, vol. 7, p. 15176.

    Article  CAS  Google Scholar 

  27. Alanthadka, A., Devi, E.S., Nagarajan, S., Sridharan, V., Suvitha, A., and Maheswari, C.U., Eur. J. Org. Chem., 2016, no. 28, p. 4872.

    Article  CAS  Google Scholar 

  28. Yang, Y. and Ma, H., Tetrahedron Lett., 2016, vol. 57, p. 5278.

    Article  CAS  Google Scholar 

  29. Wang, H., Wang, Z., Huang, H., Tan, J., and Xu, K., Org. Lett., 2016, vol. 18, p. 5680.

    Article  CAS  PubMed  Google Scholar 

  30. Shen, D., Miao, C., Wang, S., Xia, C., and Sun, W., Org. Lett., 2014, vol. 16, p. 1108.

    Article  CAS  PubMed  Google Scholar 

  31. Rudenko, A.P., Zh. Org. Khim., 1994, vol. 30, p. 1847.

    CAS  Google Scholar 

  32. Rudenko, A.P. and Pragst, F., Russ. J. Org. Chem., 1998, vol. 34, p. 1589.

    CAS  Google Scholar 

  33. Vasilyev, A.V., Mini-Rev. Org. Chem., 2017, vol. 14, p.204.

    Article  CAS  Google Scholar 

  34. Todres, Z.V., Ion-Radical Organic Chemistry: Principles and Applications, Boca Raton: CRC, 2009, 2nd ed.

    Google Scholar 

  35. Carter, D.V., Charlton, P.T., Fenton, A.H., Housley, J.R., and Lessel, B., J. Pharm. Pharmacol., 1958, vol. 10, p.149.

    Article  CAS  PubMed  Google Scholar 

  36. Wessig, P. and Teubner, J., Synlett, 2006, p. 1543.

    Google Scholar 

  37. Kawate, T., Iwase, N., Shimizu, M., Stanley, S., Wellington, S., Kazyanskaya, E., and Hung, D.T., Bioorg. Med. Chem. Lett., 2013, vol. 23, p. 6052.

    Article  CAS  PubMed  Google Scholar 

  38. Steiner, K.U., Helv. Chim. Acta, 1952, vol. 35, p. 2486.

    Article  CAS  Google Scholar 

  39. Beinhoff, M., Weigel, W., Jurczok, M., Rettig, W., Modrakowski, C., Brudgam, I., Hartl, H., and Schluter, A.D., Eur. J. Org. Chem., 2001, p. 3819.

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. St. Petersburg State Forest Technical University, Institutskii per. 5, St. Petersburg, 194021, Russia

    M. A. Sandzhieva, E. S. Aryamova, E. V. Grinenko & A. V. Vasilyev

  2. Magnetic Resonance Research Center, St. Petersburg State University, Universitetskii pr. 26, St. Petersburg, 198504, Russia

    S. M. Sukharzhevskii

  3. Institute of Chemistry, St. Petersburg State University, Universitetskii pr. 26, St. Petersburg, 198504, Russia

    A. V. Vasilyev

Authors
  1. M. A. Sandzhieva
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. E. S. Aryamova
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. S. M. Sukharzhevskii
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. E. V. Grinenko
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. A. V. Vasilyev
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to A. V. Vasilyev.

Additional information

Dedicated to Full Member of the Russian Academy of Sciences

I.P. Beletskaya on her jubilee

Original Russian Text © M.A. Sandzhieva, E.S. Aryamova, S.M. Sukharzhevskii, E.V. Grinenko, A.V. Vasilyev, 2018, published in Zhurnal Organicheskoi Khimii, 2018, Vol. 54, No. 3, pp. 393–398.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Sandzhieva, M.A., Aryamova, E.S., Sukharzhevskii, S.M. et al. Oxidation of Iodo- and Bromo-Substituted Polymethylbenzenes in the System PbO2–CF3COOH–CH2Cl2. Russ J Org Chem 54, 397–402 (2018). https://doi.org/10.1134/S1070428018030053

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070428018030053

Search

Navigation