Skip to main content
SpringerLink
Log in

Interaction of 9-substituted anthracenes with oxidation systems tert-butylhydroperoxide-metal tert-butoxide

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

Abstract

9-R-Anthracenes (R = Me, Ph) are effective acceptors of peroxyl and metalalkoxyl radicals in the systems tert-butylhydroperoxide-metal tert-butoxide (M = Al, V, Cr; C6H6, 20°C). Isolation of 9-R-9,10-dihydro-9,10-di-tert-butylperoxyanthracenes, 10-R-10-tert-butylperoxy-9-anthrones as major products reliably confirms the formation of tert-butylperoxy radicals and can be used for quantitative assessment of their content.

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. Stepovik, L.P., Martinova, I.M., Dodonov, V.A., and Cherkasov, V.K., Russ. Chem. Bull., 2002, vol. 51, no. 4, p. 638. DOI: 10.1023/A:1015812016868.

    Article  CAS  Google Scholar 

  2. Stepovik, L.P., Gulenova, M.V., Martinova, I.M., Mar’yasin, B.A., and Cherkasov, V.K., Russ. J. Gen. Chem., 2008, vol. 78, no. 2, p. 266. DOI: 10.1134/s1070363208020151.

    Article  CAS  Google Scholar 

  3. Stepovik, L.P., Gulenova, M.V., and Martinova, I.M., Russ. J. Gen. Chem., 2005, vol. 75, no. 4, p. 507. DOI:10.1007/s11176-005-0262-6.

    Article  CAS  Google Scholar 

  4. Stepovik, L.P., Gulenova, M.V., Tishkina, A.N., and Cherkasov, V.K., Russ. J. Gen. Chem., 2007, vol. 77, no. 7, p. 1254. DOI: 10.1134/s1070363207070183.

    Article  CAS  Google Scholar 

  5. Gulenova, M.V., Stepovik, L.P., and Cherkasov, V.K., Russ. J. Gen. Chem., 2006, vol. 76, no. 6, p. 980. DOI:10.1134/s1070363206060235.

    Article  CAS  Google Scholar 

  6. Stepovik, L.P., Potkina, A.Yu., and Poddelskii, A.I., Russ. J. Gen. Chem., 2013, vol. 83, no. 11, p. 2005. DOI: 10.1134/s1070363213110066.

    Article  CAS  Google Scholar 

  7. Főrster, S., Rieker, A., Maryama, K., Murata, K., and Nishigana, A., J. Org. Chem., 1996, vol. 61, no. 10, p. 3320. DOI: 10.1021/jo952198p.

    Article  Google Scholar 

  8. Pokhodenko, V.D., Ganyuk, L.N., and Brodskii, A.I., Dokl. Akad. Nauk SSSR, 1962, vol. 145, no. 4, p. 815.

    CAS  Google Scholar 

  9. Bartlett, P.D. and Gunter, P., J. Am. Chem. Soc., 1966, vol. 88, no. 14, p. 3288. DOI: 10.1021/ja1492a055.

    Article  CAS  Google Scholar 

  10. Campbell, B.T.W. and Coppinger, G.M., J. Am. Chem. Soc., 1952, vol. 74, no. 6, p. 1469. DOI: 10.1021/ja01126a032.

    Article  CAS  Google Scholar 

  11. Stepovik, L.P. and Potkina, A.Yu., Russ. J. Gen. Chem., 2013, vol. 83, no. 6, p. 1047. DOI: 10.1134/s1070363213060078.

    Article  CAS  Google Scholar 

  12. Hiatt, R., Clipsham, J., and Visser, T., Canad. J. Chem., 1964, vol. 42, no. 12, p. 2754. DOI: 10.1139/v64-408.

    Article  CAS  Google Scholar 

  13. Groysman, S., Villagram, D., and Nocera, D.G., Inorg. Chem., 2010, vol. 49, no. 23, p. 10759. DOI: 10.1021/ic101968s.

    Article  CAS  Google Scholar 

  14. Kotani, H., Ohkubo, K., and Fukuzumi, S., J. Am. Chem. Soc., 2004, vol. 126, no. 49, p. 15999. DOI:10.1021/ja048353b.

    Article  CAS  Google Scholar 

  15. Antonovskii, V.L. and Khursan, S.L., Fizicheskaya khimiya organicheskikh peroksidov (Physical Chemistry of Organic Peroxides), Moscow: Akademkhiga, 2003, p. 92.

    Google Scholar 

  16. Stepovik, L.P. and Gulenova, M.V., Russ. J. Gen. Chem., 2009, vol. 79, no. 8, p. 1663. DOI: 10.1134/s1070363209080143.

    Article  CAS  Google Scholar 

  17. Palmer, W.G., Experimental Inorganic Chemistry, Cambridge; New York: Cambridge University Press, 1954, p. 385.

    Google Scholar 

  18. Sheldrick, G.M., SHELXTL v. 6.14, Structure Determination Software Suite, Bruker AXS, Madison, Wisconsin, USA, 2003.

    Google Scholar 

  19. Sheldrick, G.M., SADABS v.2014/1, Bruker/Siemens Area Detector Absorption Correction Program, Bruker AXS, Madison, Wisconsin, USA, 2014.

    Google Scholar 

  20. Bradly, D.C. and Mehta, M.L., Canad. J. Chem. 1962, vol. 40, no. 6, p. 1183.

    Article  Google Scholar 

  21. Krauss, H.-L. and Munster, G., Z. Anorg. Allg. Chem., 1967, vol. 352, no. 1, p. 24.

    Article  CAS  Google Scholar 

  22. Alyea, E.C., Basi, J.S., Bradley, D.C., and Chisholm, M.H., J. Chem. Soc. (A), 1971, part 1, p. 772.

    Google Scholar 

  23. Southern, P.E. and Waters, W.A., J. Chem. Soc., 1960, no. 11, p. 434.

    Google Scholar 

  24. Bartlett, P.D., Benzing, E.P., and Pincock, R.E., J. Am. Chem. Soc. 1960, vol. 82, no. 7, p. 1762. DOI: 10.1021/ja1492a055.

    Article  CAS  Google Scholar 

  25. Moiseeva, N.I., Gekhman, A.E., Minin, V.V., Larin, G.M., Baskhtanov, M.E., Krasnovskii, A.E., and Moiseev, I.I., Kinet. Katal., 2000, vol. 41, no. 2, p. 191.

    Article  Google Scholar 

  26. Donkers, R.L. and Workentin, M.S., J. Am. Chem. Soc., 2004, vol. 126, no. 6, p. 1688.

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Lobachevsky State University of Nizhny Novgorod, pr. Gagarina 23, Nizhny Novgorod, 603950, Russia

    L. P. Stepovik, Yu. B. Malysheva & G. K. Fukin

  2. Razuvaev Institute of Organometallic Chemistry of Russian Academy of Sciences, Nizhny Novgorod, Russia

    G. K. Fukin

Authors
  1. L. P. Stepovik
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Yu. B. Malysheva
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. G. K. Fukin
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to L. P. Stepovik.

Additional information

Original Russian Text © L.P. Stepovik, Yu.B. Malysheva, G.K. Fukin, 2015, published in Zhurnal Obshchei Khimii, 2015, Vol. 85, No. 6, pp. 933–943.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Stepovik, L.P., Malysheva, Y.B. & Fukin, G.K. Interaction of 9-substituted anthracenes with oxidation systems tert-butylhydroperoxide-metal tert-butoxide. Russ J Gen Chem 85, 1401–1411 (2015). https://doi.org/10.1134/S1070363215060080

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070363215060080

Keywords

Search

Navigation