Skip to main content
SpringerLink
Log in

Synthesis, Structure, and Electrochemical Properties of New Sterically Hindered o-Benzoquinone—6,9-Di-tert-Butyl-1,2,3a,4-Tetrahydrobenzo[b]oxazolo[3,2-d][1,4]oxazine-7,8-Dione

  • STRUCTURE OF ORGANIC COMPOUNDS
  • Published:
Crystallography Reports Aims and scope Submit manuscript

Abstract

A new representative of sterically hindered 3,6-di-tert-butyl-o-benzoquinones bearing an annulated tetrahydrooxazolo[3,2-d][1,4]oxazine moiety—6,9-di-tert-butyl-1,2,3a,4-tetrahydrobenzo[b]oxazolo[3,2-d][1,4]oxazine-7,8-dione—was synthesized. The structure of the novel compound was confirmed by IR, UV, and NMR spectroscopy and X-ray diffraction. According to the cyclic voltammetry, the first reduction potential of the quinone in acetonitrile is –0.83 V (Ag/AgCl/KCl reference electrode).

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

Fig. 1.
Fig. 2.
Fig. 3.
Fig. 4.

Similar content being viewed by others

REFERENCES

  1. N. Y. Shushunova and S. A. Chesnokov, Polym. Sci. B 51, 427 (2009).

    Google Scholar 

  2. S. A. Chesnokov, M. V. Arsenyev, R. S. Kovylin, et al., Appl. Organomet. Chem. 31, e3553 (2017).

    Article  Google Scholar 

  3. S. A. Chesnokov, V. K. Cherkasov, G. A. Abakumov, et al., Polym. Sci. B 56, 11 (2014).

    Google Scholar 

  4. A. I. Konovalov, I. S. Antipin, V. A. Burilov, et al., Russ. J. Org. Chem. 54, 157 (2018).

    Article  Google Scholar 

  5. G. A. Abakumov, V. K. Cherkasov, T. N. Kocherova, et al., Russ. Chem. Bull. 55, 1195 (2006).

    Article  Google Scholar 

  6. T. I. Prokof’eva, V. B. Vol’eva, A. I. Prokof’ev, et al., Chem. Heterocycl. Compd. 36, 923 (2000).

    Article  Google Scholar 

  7. M. Kicsak, A. Mandi, S. Varga, et al., Org. Biomol. Chem. 16, 393 (2018).

    Article  Google Scholar 

  8. B. Alcaide, S. Garcia-Blanco, M. T. Garcia-Gonzalez, et al., Tetrahedron Lett. 27, 4217 (1986).

    Article  Google Scholar 

  9. Bruker, SMART-Bruker Molecular Analysis Research Tool, v. 5.632 (Bruker AXS, Madison, 2005).

  10. Bruker, SAINTPlus Data Reduction and Correction Program, v. 6.45a (Bruker AXS, Madison, 2003).

  11. G. M. Sheldrick, TWINABS, v. 2012/1. Bruker/Siemens Area Detector Absorption Correction Program for Twinned Crystals (Bruker AXS, Madison, 2012).

  12. G. M. Sheldrick, SHELXTL, v. 6.14. Structure Determination Software Suite (Bruker AXS, Madison, 2003).

  13. O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, et al., J. Appl. Crystallogr. 42, 339 (2009).

    Article  Google Scholar 

  14. G. A. Abakumov, V. K. Cherkasov, T. N. Kocherova, et al., Russ. Chem. Bull. 56, 1849 (2007).

    Article  Google Scholar 

  15. I. V. Smolyaninov, V. V. Kuzmin, M. V. Arsenyev, et al., Russ. Chem. Bull. 66, 1217 (2017).

    Article  Google Scholar 

  16. V. K. Cherkasov, G. A. Abakumov, E. V. Grunova, et al., Chem. Eur. J. 12, 3916 (2006).

    Article  Google Scholar 

  17. A. I. Poddel’sky, I. V. Smolyaninov, Y. A. Kurskii, et al., J. Organomet. Chem. 695, 1215 (2010).

    Article  Google Scholar 

  18. M. P. Bubnov, N. A. Skorodumova, E. V. Baranov, et al., Inorg. Chim. Acta 392, 84 (2012).

    Article  Google Scholar 

Download references

ACKNOWLEDGMENTS

This study performed within the framework of the state assignment using equipment of the Analytical Center of the Razuvaev Institute of Organometallic Chemistry of the Russian Academy of Sciences.

Author information

Authors and Affiliations

  1. Razuvaev Institute of Organometallic Chemistry, Russian Academy of Sciences, 603950, Nizhny Novgorod, Russia

    M. V. Arsenyev, E. A. Chelnokov, E. V. Baranov & S. A. Chesnokov

Authors
  1. M. V. Arsenyev
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. E. A. Chelnokov
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. E. V. Baranov
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. S. A. Chesnokov
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to M. V. Arsenyev.

Additional information

Translated by T. Safonova

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Arsenyev, M.V., Chelnokov, E.A., Baranov, E.V. et al. Synthesis, Structure, and Electrochemical Properties of New Sterically Hindered o-Benzoquinone—6,9-Di-tert-Butyl-1,2,3a,4-Tetrahydrobenzo[b]oxazolo[3,2-d][1,4]oxazine-7,8-Dione. Crystallogr. Rep. 65, 253–257 (2020). https://doi.org/10.1134/S1063774520020030

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1063774520020030

Search

Navigation