Skip to main content
SpringerLink
Log in

Cobalt-catalyzed bisperoxidation of styrenes

  • Full Articles
  • Published:
Russian Chemical Bulletin Aims and scope

Abstract

A cobalt-catalyzed peroxidation of styrenes with tert-butyl hydroperoxide gives 1-aryl-1,2-bis(tert-butylperoxy)ethanes in up to 53% yields.

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. (a) D. M. Opsenica, B. A. Solaja, J. Serb. Chem. Soc., 2009, 74, 1155–1193

    Article  CAS  Google Scholar 

  2. P. Ghorai, P. H. Dussault, C. Hu, Org. Lett., 2008, 10, 2401–2404

    Article  CAS  Google Scholar 

  3. Y. Dong, Mini-Rev. Med. Chem., 2002, 2, 113–123

    Article  CAS  Google Scholar 

  4. J. L. Vennerstrom, H.-N. Fu, W. Y. Ellis, A. L. Ager, J. K. Wood, S. L. Andersen, L. Gerena, W. K. Milhous, J. Med. Chem. (Engl. Transl.), 1992, 35, 3023–3027

    CAS  Google Scholar 

  5. N. Yadav, C. Sharma, S. K. Awasthi, RSC Adv., 2014, 4, 5469–5498

    Article  CAS  Google Scholar 

  6. A. O. Terent′ev, D. A. Borisov, I. A. Yaremenko, Chem. Heterocycl. Compd., 2012, 48, 55–58 [Khim. Geterotsikl. Soedin., 2012, 60–63]

    Article  Google Scholar 

  7. E. T. Denisov, S. L. Solodova, T. G. Denisova, Russ. Chem. Rev., 2010, 79, 981–1003.

    Article  CAS  Google Scholar 

  8. (a) J. Keiser, V. Veneziano, L. Rinaldi, L. Mezzino, U. Duthaler, G. Cringoli, Res. Vet. Sci., 2010, 88, 107–110

    Article  CAS  Google Scholar 

  9. X. Shuhua, M. Tanner, E. K. N′Goran, J. Utzinger, J. Chollet, R. Bergquist, C. Minggang, Z. Jiang, Acta Trop., 2002, 82, 175–181

    Article  Google Scholar 

  10. K. Ingram, I. A. Yaremenko, I. B. Krylov, L. Hofer, A. O. Terent′ev, J. Keiser, J. Med. Chem., 2012, 55, 8700–8711.

    Article  CAS  Google Scholar 

  11. (a) N. Kumar, M. Sharma, D. S. Rawat, Curr. Med. Chem., 2011, 18, 3889–3928

    Article  CAS  Google Scholar 

  12. Z. Zizak, Z. Juranic, D. Opsenica, B. A. Solaja, Invest. New Drugs, 2009, 27, 432–439

    Article  CAS  Google Scholar 

  13. N. Terzic, D. Opsenica, D. Milic, B. Tinant, K. S. Smith, W. K. Milhous, B. A. Solaja, J. Med. Chem., 2007, 50, 5118–5127.

    Article  CAS  Google Scholar 

  14. (a) M. S. Kharasch, P. Pauson, W. Nudenberg, J. Org. Chem., 1953, 18, 322–327

    Article  CAS  Google Scholar 

  15. M. S. Kharasch, A. Fono, J. Org. Chem., 1958, 23, 324–325.

    Google Scholar 

  16. (a) G. B. Shul’pin, J. Gradinaru, Y. N. Kozlov, Org. Biomol. Chem., 2003, 1, 3611–3617

    Article  Google Scholar 

  17. S. Araneo, F. Fontana, F. Minisci, F. Recupero, A. Serri, J. Chem. Soc., Chem. Commun., 1995, 1399–1400

    Google Scholar 

  18. A. O. Terent′ev, D. A. Borisov, I. A. Yaremenko, V. V. Chernyshev, G. I. Nikishin, J. Org. Chem., 2010, 75, 5065–5071

    Article  Google Scholar 

  19. A. O. Terent′ev, D. A. Borisov, V. V. Semenov, V. V. Chernyshev, V. M. Dembitsky, G. I. Nikishin, Synthesis, 2011, 2091–2100

    Google Scholar 

  20. A. O. Terent′ev, V. A. Vil′, O. V. Bityukov, G. I. Nikishin, Russ. Chem. Bull. (Int. Ed.), 2014, 63, 2461–2466 [Izv. Akad. Nauk, Ser. Khim., 2014, 2461–2466].

    Article  Google Scholar 

  21. L. Saussine, E. Brazi, A. Robine, H. Mimoun, J. Fischer, R. Weiss, J. Am. Chem. Soc., 1985, 107, 3534–3540.

    Article  CAS  Google Scholar 

  22. (a) T. Kojima, R. A. Leising, S. Yan, L. Que, Jr., J. Am. Chem. Soc., 1993, 115, 11328–11335

    Article  CAS  Google Scholar 

  23. I. W. C. E. Arends, K. U. Ingold, D. D. M. Wayner, J. Am. Chem. Soc., 1995, 117, 4710–4711

    Article  CAS  Google Scholar 

  24. F. Minisci, F. Fontana, S. Araneo, F. Recupero, J. Chem. Soc., Chem. Commun., 1994, 1823–1824.

    Google Scholar 

  25. (a) A. O. Terent′ev, M. Yu. Sharipov, I. B. Krylov, D. V. Gaidarenko, G. I. Nikishin, Org. Biomol. Chem., 2015, 13, 1439–1445

    Article  Google Scholar 

  26. F. Minisci, F. Fontana, S. Araneo, F. Recupero, S. Banfi, S. Quici, J. Am. Chem. Soc., 1995, 117, 226–232.

    Article  CAS  Google Scholar 

  27. (a) J. Q. Yu, E. J. Corey, Org. Lett., 2002, 4, 2727–2730

    Article  CAS  Google Scholar 

  28. G. An, W. Zhou, G. Zhang, H. Sun, J. Han, Y. Pan, Org. Lett., 2010, 12, 4482–4485.

    Article  CAS  Google Scholar 

  29. (a) S.-I. Murahashi, D. Zhang, Chem. Soc. Rev., 2008, 37, 1490–1501

    Article  CAS  Google Scholar 

  30. S.-I. Murahashi, T. Naota, T. Kuwabara, T. Saito, H. Kumobayashi, S. Akutagawa, J. Am. Chem. Soc., 1990, 112, 7820–7822.

    Article  CAS  Google Scholar 

  31. T. Nishimura, T. Onoue, K. Ohe, J. I. Tateiwa, S. Uemura, Tetrahedron Lett., 1998, 39, 4359–4362.

    Article  CAS  Google Scholar 

  32. M. T. Rispens, O. J. Gelling, A. M. de Vries, A. Meetsma, F. van Bolhuis, B. L. Feringa, Tetrahedron, 1996, 52, 3521–3546.

    Article  CAS  Google Scholar 

  33. (a) G. I. Nikishin, A. V. Aleksandrov, A. V. Ignatenko, E. K. Starostin, Bull. Acad. Sci. USSR, Div. Chem. Sci. (Engl. Transl.), 1984, 33, 2407–2409 [Izv. Akad. Nauk SSSR, Ser. Khim., 1984, 2628–2630]

    Article  Google Scholar 

  34. F. Minisci, A. Portolani, Gazz. Chim. Ital., 1959, 89, 1922–1937

    CAS  Google Scholar 

  35. Yu. N. Ogibin, E. K. Starostin, A. V. Aleksandrov, K. K. Pivnitsky, G. I. Nikishin, Synthesis, 1994, 901–903

    Google Scholar 

  36. O. Blank, N. Raschke, M. R. Heinrich, Tetrahedron Lett., 2010, 51, 1758–1760

    Article  CAS  Google Scholar 

  37. A. Prechter, M. R. Heinrich, Synthesis, 2011, 10, 1515–1525

    Google Scholar 

  38. Yu. N. Ogibin, A. O. Terent′ev, V. P. Ananikov, G. I. Nikishin, Russ. Chem. Bull. (Int. Ed.), 2001, 50, 2149–2155 [Izv. Akad. Nauk, Ser. Khim. 2001, 2052–2057]

    Article  CAS  Google Scholar 

  39. A. Masuyama, T. Sugawara, M. Nojima, K. J. McCullough, Tetrahedron, 2003, 53, 353–366.

    Article  Google Scholar 

  40. (a) L. Saussine, E. Brazi, A. Robine, H. Mimoun, J. Fischer, R. Weiss, J. Am. Chem. Soc., 1985, 107, 3534–3540

    Article  CAS  Google Scholar 

  41. R. P. Houghton, C. R. Rice, Polyhedron, 1996, 15, 1893–1897

    Article  CAS  Google Scholar 

  42. F. A. Chavez, P. K. Mascharak, Acc. Chem. Res., 2000, 33, 539–545

    Article  CAS  Google Scholar 

  43. E. Watanabe, A. Kaiho, H. Kusama, N. Iwasawa, J. Am. Chem. Soc., 2013, 135, 11744–11747.

    Article  CAS  Google Scholar 

  44. S. Albert, R. Horbach, H. B. Deising, B. Siewert, R. Csuk, Bioorg. Med. Chem., 2011, 19, 5155–5166.

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991, Moscow, Russian Federation

    A. O. Terent´ev, M. Yu. Sharipov & G. I. Nikishin

  2. D. I. Mendeleev University of Chemical Technology of Russia, 9 Miusskaya pl., 125047, Moscow, Russian Federation

    A. O. Terent´ev & M. Yu. Sharipov

Authors
  1. A. O. Terent´ev
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. M. Yu. Sharipov
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. G. I. Nikishin
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to A. O. Terent´ev.

Additional information

On the occasion of the 100th anniversary of the birth of Academician N. K. Kochetkov (1915—2005).

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 5, pp. 1053—1056, May, 2015.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Terent´ev, A.O., Sharipov, M.Y. & Nikishin, G.I. Cobalt-catalyzed bisperoxidation of styrenes. Russ Chem Bull 64, 1053–1056 (2015). https://doi.org/10.1007/s11172-015-0975-6

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11172-015-0975-6

Keywords

Search

Navigation