Russian Journal of Organic Chemistry

, Volume 49, Issue 3, pp 446–449 | Cite as

Antiradical activity of dioxolane derivatives

  • V. B. Vol’eva
  • I. S. Belostotskaya
  • N. L. Komissarova
  • A. V. Malkova
  • T. V. Pokholok
  • E. Ya. Davydov
Article

Abstract

1,3-Benzodioxoles synthesized by condensation of 3,6-di-tert-butylbenzene-1,2-diol with carbonyl compounds showed antiradical activity due to their ability to undergo one-electron oxidation with formation of stable radical cations. On this basis, the antiknock effect of their structural analogs, 1,3-dioxolanes derived from vicinal diols, was interpreted in terms of oxidation of these compounds with active radicals generated from fuel hydrocarbons to produce more stable radical or radical ion species, depending on the fuel composition. The formation of radical species was detected in model oxidation reactions of 2,2-dimethyl-1,3-dioxolane and 2,2-dimethyl-1,3-dioxolan-4-ylmethanol with radicals generated by photolysis of iron(III) chloride and benzoyl peroxide.

Keywords

Radical Cation Benzoyl Peroxide Antiradical Activity Hyperfine Coupling Constant Vicinal Diol 

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. 1.
    Varbanskaya, R.A., Pudov, V.S., Komissarova, N.L., Belostotskaya, I.S., Vol’eva, V.B., and Ershov, V.V., USSR Inventor’s Certificate no. 1 143 752, 1984; Byull. Izobret., 1985, no. 9.Google Scholar
  2. 2.
    Malysheva, N.N., Prokof’ev, A.I., Solodovnikov, S.P., Bubnov, N.N., Prokof’eva, T.I., Vol’eva, V.B., Ershov, V.V., and Kabachnik, M.I., Izv. Akad. Nauk SSSR, Ser. Khim., 1988, p. 1040.Google Scholar
  3. 3.
    Vol’eva, V.B., Belostotskaya, I.S., Novikova, I.A., Dzhuaryan, E.V., and Ershov, V.V., Izv. Akad. Nauk SSSR, Ser. Khim., 1980, p. 2414.Google Scholar
  4. 4.
    Komissarova, N.L., Belostotskaya, I.S., Vol’eva, V.B., Dzhuaryan, E.V., Novikova, I.A., and Ershov, V.V., Izv. Akad. Nauk SSSR, Ser. Khim., 1981, p. 2360.Google Scholar
  5. 5.
    Varfolomeev, S.D., Nikiforov, G.A., Vol’eva, V.B., Makarov, G.G., and Trusov, L.I., Russian Patent no. 2 365 617, 2009; Byull. Izobret., 2009, no. 24.Google Scholar
  6. 6.
    Pokholok, T.V., Zaitseva, N.I., Pariysky, G.B., and Toptygin, D.Ya., Polym. Photochem., 1982, vol. 2, p. 429.CrossRefGoogle Scholar
  7. 7.
    Pariiskii, G.B., Toptygin, D.Ya., Davydov, E.Ya., Ledneva, O.A., Mikheev, Yu.A., and Karasev, V.M., Vysokomol. Soedin., Ser. B, 1972, vol. 14, p. 511.Google Scholar
  8. 8.
    Pshezhetskii, S.Ya., Kotov, A.G., Milinchuk, V.K., Roginskii, V.A., and Tupikov, V.I., EPR svobodnykh radikalov v radiatsionnoi khimii (ESR of Free Radicals in Radiation Chemistry), Moscow: Khimiya, 1972, p. 52.Google Scholar
  9. 9.
    Dyment, O.N., Kazanskii, K.S., and Miroshnikov, A.M., Glikoli i drugie proizvodnye okisi etilena i propilena (Glycols and Other Derivatives of Ethylene and Propylene Oxides), Dyment, O.N., Ed., Moscow: Khimiya, 1976, p. 121.Google Scholar
  10. 10.
    Kasaikina, O.T., Kartasheva, Z.S., and Pisarenko, L.M., Russ. J. Gen. Chem., 2008, vol. 78, p. 1533.CrossRefGoogle Scholar
  11. 11.
    Vol’eva, V.B., Novikova, I.A., Ostapets-Sveshnikova, G.D., Belostotskaya, I.S., and Ershov, V.V., Izv. Akad. Nauk SSSR, Ser. Khim., 1980, p. 2416.Google Scholar
  12. 12.
    Dzhuaryan, E.V., Belostotskaya, I.S., and Ershov, V.V., Izv. Akad. Nauk SSSR, Ser. Khim., 1973, p. 658.Google Scholar

Copyright information

© Pleiades Publishing, Ltd. 2013

Authors and Affiliations

  • V. B. Vol’eva
    • 1
  • I. S. Belostotskaya
    • 1
  • N. L. Komissarova
    • 1
  • A. V. Malkova
    • 1
  • T. V. Pokholok
    • 1
  • E. Ya. Davydov
    • 1
  1. 1.Emanuel’ Institute of Biochemical PhysicsRussian Academy of SciencesMoscowRussia

Personalised recommendations