Skip to main content
Log in

Reaction of 3,4,6-Triisopropyl-о-benzoquinone with 3,4,6-Triisopropylcatechol

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

Abstract

Formation of protonated 3,4,6-triisopropylsemiquinone radicals in solution of a mixture of 3,4,6- triisopropyl-о-benzoquinone and 3,4,6-triisopropylcatechol was shown using ESR spectroscopy. Heating the mixture to 110°С leads to the formation of the condensation products, additional amount of 3,4,6-triisopropylcatechol, and evolution of propylene. Mathematical simulation of the kinetics of the reaction was performed.

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

Access this article

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

Instant access to the full article PDF.

Similar content being viewed by others

References

  1. Pointillart, F., Klementieva, S., Kuropatov, V., Le Gal, Y., Golhen, S., Cador, O., Cherkasov, V., and Ouahab, L., Chem. Commun., 2012, vol. 48, p. 714. doi 10.1039/c1cc16314k

    Article  CAS  Google Scholar 

  2. Minkin, V.I., Starikova, A.A., and Starikov, A.G., Dalton Trans., 2015, vol. 44, p. 1982. doi 101039/4dt03053b

    Article  CAS  PubMed  Google Scholar 

  3. Haoyuan Li, Chavez, A.D., Huifang Li, Hong Li, Dichtel, W.R., and Bredas, J.-L., J. Am. Chem. Soc., 2017, vol. 139, p. 16310. doi 10.1021/jacs.7b09169

    Article  CAS  Google Scholar 

  4. Thompson, C.M., Occhialini, G., Mc Candless, G.T., Alahakoon, S.B., Cameron, V., Nielsen, S.O., and Smaldone, R.A., J. Am. Chem. Soc., 2017, vol. 139, p. 10506. doi 10.1021/jacs.7b05555

    Article  CAS  PubMed  Google Scholar 

  5. Zemtsova, O.V. and Zheleznov, K.N., Russ. Chem. Bull., 2004, vol. 53, no. 8, p. 1743. doi 10.1007/s11172-005-0028-7

    Article  CAS  Google Scholar 

  6. Zagorskii, A.L., Kalnin’sh, K.K., and Toropov, D.K., Russ. J. Appl. Chem., 2005, vol. 78, no. 8, p. 656. doi 10.1007/s11167-005-0363-3

    Article  CAS  Google Scholar 

  7. Liogon’kii, B.I., Ragimov, A.V., Bektashi, F.T., and Nagiev, A.Yu., Dokl. Akad. Nauk SSSR, 1982, vol. 266, no. 4, p. 903.

    Google Scholar 

  8. Love, B.E., Duffy, B.C., and Simmons, A.L., Tetrahedron Lett., 2014, vol. 55, no. 12, p. 1994. doi 10.1016/j.tetlet.2014.02.17

    Article  CAS  Google Scholar 

  9. Abakumov, G.A., Nevodchikov, V.L., Druzhkkov, N.O., Zakharov, L.N., Abakumova, L.G., Kurskii, Yu.A., and Cherkasov, V.K., Russ. Chem. Bull., 1997, vol. 46, no. 4, p. 771. doi 10.1007/BF02495211

    Article  CAS  Google Scholar 

  10. Pokhodenko, V.D., Fenoksil’nye radikaly (Phenoxy Radicals), Kyiv: Naukova Dumka, 1969.

    Google Scholar 

  11. Cook, C.D. and Norcross, B.E., J. Am. Chem. Soc., 1956, vol. 78, no. 15, p. 3797. doi 10.1021/ja01596a064

    Article  CAS  Google Scholar 

  12. Bodrikov, I.V., Grinval’d, I.I., Subbotin, A.Yu., Druzhkov, N.O., and Kocherova, T.N., Doklady Chem., 2013, vol. 448, no. 1, p. 19. doi 10.7868/S0869565213030134

    Article  CAS  Google Scholar 

  13. Gurvich, L.V., Karachentsev, G.V., Kondrat’ev, Yu.A., Lebedev, Yu.A., Medvedev V.A., Potapov, V.K., and Khodeev, Yu.S., Energii razryva khimicheskikh svyazei. Potentsialy ionizatsii i srodstvo k elektronu (The Energy of Rupture of Chemical Bonds. Potentials of Ionization and Electron Affinity), Moscow: Nauka, 1974.

    Google Scholar 

  14. Zavelovich, E.B. and Prokof’ev, A.I., Chem. Phys. Lett., 1974, vol. 29, no. 2, p. 212. doi 10.1016/0009-2614(74) 85015-3

    Article  CAS  Google Scholar 

  15. Abakumov, G.A., Vavilina, N.N., Kurskii, Yu.A., Nevodchikov, V.I., Cherkasov, V.K., and Shavyrin, A.S., Russ. Chem. Bull., 2003, vol. 52, no. 8, p. 1847. doi 10.1023/A:1026029410312

    Article  CAS  Google Scholar 

  16. Cherkasov, V.K., Abakumov, G.A., Shavyrin, A.S., Kuz’michev, V.V., Baranov, E.V., Smolyaninov, I.V., and Kuropatov, V.A., Asian. J. Org. Chem., 2015, vol. 4, no. 5, p. 446. doi 10.1002/ajoc.201500005

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Yu. A. Kurskii.

Additional information

Original Russian Text © Yu.А. Kurskii, А.S. Shavyrin, Т.I. Kulikova, V.А. Kuropatov, G.А. Abakumov, 2018, published in Zhurnal Obshchei Khimii, 2018, Vol. 88, No. 8, pp. 1262–1267.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Kurskii, Y.A., Shavyrin, A.S., Kulikova, T.I. et al. Reaction of 3,4,6-Triisopropyl-о-benzoquinone with 3,4,6-Triisopropylcatechol. Russ J Gen Chem 88, 1584–1589 (2018). https://doi.org/10.1134/S1070363218080054

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070363218080054

Keywords

Navigation