Skip to main content
SpringerLink
Log in

Mechanism of electrochemical reduction of 5-thio derivatives of 2(5H)-furanone

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

Abstract

The anionoid elimination of the substituent from position 5 of the lactone ring is the predominant pathway of electrochemical reduction of 5-arylsulfanyl- and 5-arylsulfonyl-3,4-dichloro-2(5H)-furanones in acetonitrile. The contribution of the competing elimination of the chloride ion increases on going to 3,4-dichloro-5-ethylsulfanyl-2(5H)-furanone. An experimental criterion based on the morphology of cyclic voltammograms was proposed for identification of a particular pathway of electroreduction of 2(5H)-furanone derivatives.

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. J. Zhang, K. D. Sarma, T. T. Curran, Synlett, 2013, 24, 550.

    Article  Google Scholar 

  2. K. Biswas, R. Gholap, P. Srinivas, S. Kanyal, K. Das Sarma, RSC Adv., 2014, 4, 2538.

    Article  CAS  Google Scholar 

  3. A. R. Kurbangalieva, O. A. Lodochnikova, N. F. Devyatova, E. A. Berdnikov, O. I. Gnezdilov, I. A. Litvinov, G. A. Chmutova, Tetrahedron, 2010, 66, 9945.

    Article  CAS  Google Scholar 

  4. F. Bellina, R. Rossi, Curr. Org. Chem., 2004, 8, 1089.

    Article  CAS  Google Scholar 

  5. A. A. Avetisyan, M. T. Dangyan, Russ. Chem. Rev., 1977, 46, 643.

    Article  Google Scholar 

  6. D. W. Knight, Contemp. Org. Synth., 1994, 1, 287.

    Article  CAS  Google Scholar 

  7. R. Rossi, M. Lessi, C. Manzini, G. Marianetti, F. Bellina, Curr. Org. Chem., 2017, 21, 964.

    Article  CAS  Google Scholar 

  8. M. V. N. De Souza, Mini-Rev. Org. Chem., 2005, 2, 139.

    Article  CAS  Google Scholar 

  9. S. Kumar, R. Garg, A. Kabra, World J. Pharm. Res., 2013, 1, 83.

    Google Scholar 

  10. A. R. Kurbangalieva, N. F. Devyatova, A. V. Bogdanov, E. A. Berdnikov, T. G. Mannafov, D. B. Krivolapov, I. A. Litvinov, G. A. Chmutova, Phosphorus, Sulfur Silicon Relat. Elem., 2007, 182, 607.

    Article  CAS  Google Scholar 

  11. N. F. Devyatova, L. S. Kosolapova, A. R. Kurbangalieva, E. A. Berdnikov, O. A. Lodochnikova, I. A. Litvinov, G. A. Chmutova, Russ. J. Org. Chem., 2008, 44, 1225.

    Article  CAS  Google Scholar 

  12. A. R. Kurbangalieva, N. F. Devyatova, L. S. Kosolapova, O. A. Lodochnikova, E. A. Berdnikov, I. A. Litvinov, G. A. Chmutova, Russ. Chem. Bull., 2009, 58, 126.

    Article  CAS  Google Scholar 

  13. L. T. Hoang, A. R. Kurbangalieva, A. S. Ezhova, E. A. Berdnikov, G. A. Chmutova, Butlerov. Soobshch. [Butlerov Commun.] 2015, 42, 33 (in Russian).

    Google Scholar 

  14. A. R. Kurbangalieva, L. T. Hoang, O. A. Lodochnikova, M. Yu. Kuzmicheva, A. R. Pradipta, K. Tanaka, G. A. Chmutova, Russ. Chem. Bull., 2016, 65, 1278.

    Article  CAS  Google Scholar 

  15. L. Z. Latypova, E. S. Saigitbatalova, D. R. Chulakova, O. A. Lodochnikova, A. R. Kurbangalieva, E. A. Berdnikov, G. A. Chmutova, Russ. J. Org. Chem., 2014, 50, 521.

    Article  CAS  Google Scholar 

  16. L. Z. Latypova, E. Sh. Saigitbatalova, A. R. Kurbangalieva, O. A. Lodochnikova, G. A. Chmutova, Butlerov. Soobshch. [Butlerov Commun.], 2016, 45, 89 (in Russian).

    Google Scholar 

  17. I. S. Sharafutdinov, E. Y. Trizna, D. R. Baidamshina, M. N. Ryzhikova, R. R. Sibgatullina, A. M. Khabibrakhmanova, L. Z. Latypova, A. R. Kurbangalieva, E. V. Rozhina, M. Klinger-Strobel, R. F. Fakhrullin, M. W. Pletz, M. I. Bogachev, A. R. Kayumov, O. Makarewicz, Front. Microbiol., 2017, 8, 2246.

    Article  Google Scholar 

  18. N. F. Devyatova, A. R. Kurbangalieva, V. V. Yanilkin, G. A. Chmutova, Russ. Chem. Bull., 2009, 58, 908.

    Article  CAS  Google Scholar 

  19. J. Anthony, A. M. Boldi, Y. Rubin, M. Hobi, V. Gramlich, C. B. Knobler, P. Seiler, F. Diederich, Helv. Chim. Acta, 1995, 78, 13.

    Article  CAS  Google Scholar 

  20. B. A. Arbuzov, E. N. Klimovitskii, M. B. Timirbaev, Chem. Heterocycl. Compd., 1980, 16, 14.

    Article  Google Scholar 

  21. R. T. LaLonde, H. Perakyla, G. P. Cook, C. W. Dence, Environ. Toxicol. Chem., 1990, 9, 687.

    CAS  Google Scholar 

  22. J. Zhang, P. G. Blazecka, D. Belmont, J. G. Davidson, Org. Lett., 2002, 4, 4559.

    Article  CAS  Google Scholar 

  23. O. A. Lodochnikova, L. Z. Latypova, R. M. Khakimov, A. R. Kurbangalieva, D. B. Krivolapov, I. A. Litvinov, Russ. J. Struct. Chem., 2013, 54, 213.

    Article  CAS  Google Scholar 

  24. E. I. Ivanov, M. Ya. Fioshin, D. S. Gorbenko-Germanov, G. S. Solov´ev, Elektrokhimiya [Electrochemistry], 1990, 26, 503 (in Russian).

    CAS  Google Scholar 

  25. L. Z. Latypova, V. V. Yanilkin, A. R. Kurbangalieva, E. A. Berdnikov, G. A. Chmutova, Russ. Chem. Bull., 2012, 61, 568.

    Article  CAS  Google Scholar 

  26. A. Weissberger, E. S. Proskauer, J. A. Riddic, E. E. Toops, Organic Solvents. Physical Properties and Methods of Purifications, Interscience Publishers, Inc., New York–London, 1955.

    Google Scholar 

  27. O. N. Vlasov, B. N. Rybakov, L. M. Kogan, Zh. Prikl. Khim. [Russ. J. Appl. Chem.], 1968, 41, 373 (in Russian).

    CAS  Google Scholar 

  28. T. I. Bobrova, S. D. Volodkovich, S. S. Kukalenko, Zh. Obshch. Khim. [Russ. J. Gen. Chem.], 1975, 45, 1123 (in Russian).aaaaa

    CAS  Google Scholar 

  29. A. Ghorbani-Choghamarani, M. Nikoorazm, H. Goud arziafshar, A. Shokr, H. Almasi, J. Chem. Sci., 2011, 123, 453.

    Article  CAS  Google Scholar 

  30. M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, G. Scalmani, V. Barone, B. Mennucci, G. A. Petersson, H. Nakatsuji, X. Li, M. Caricato, H. P. Hratchian, A. F. Izmaylov, J. Bloino, G. Zheng, J. L. Sonnenberg, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, T. Vreven, J. A. Montgomery, Jr., J. E. Peralta, F. Ogliaro, M. Bearpark, J. J. Heyd, E. Brothers, K. N. Kudin, V. N. Staroverov, R. Kobayashi, J. Normand, K. Raghavachari, A. Rendell, J. C. Burant, S. S. Iyengar, J. Tomasi, M. Cossi, N. Rega, J. M. Millam, M. Klene, J. E. Knox, J. B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, R. L. Martin, K. Morokuma, V. G. Zakrzewski, G. A. Voth, P. Salvador, J. J. Dannenberg, S. Dapprich, A. D. Daniels, O. Farkas, J. B. Foresman, J. V. Ortiz, J. Cioslowski, D. J. Fox, GAUSSIAN 09, Version 7.0 (Revision A.2), Gaussian, Inc., Wallingford (CT), 2009.

    Google Scholar 

  31. J. Tomasi, M. Persico, Chem. Rev., 1994, 94, 2027.

    Article  CAS  Google Scholar 

  32. E. A. Berdnikov, Doctoral Thesis (Chemistry), Kazan State Univ., Kazan, 1988, 442 pp. (in Russian).

    Google Scholar 

  33. Ch. K. Mann, K. K. Barnes, Electrochemical Reactions in Nonaqueous Systems, Marcel Dekker, Inc., New York, 1970, 560 pp.

    Google Scholar 

  34. Yu. Yu. Lurie, Spravochnik po analiticheskoi khimii [Handbook on Analytic Chemistry], Khimiya, Moscow, 1989, 448 pp. (in Russian).

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. A. M. Butlerov Institute of Chemistry, Kazan Federal University, 18 ul. Kremlevskaya, 420008, Kazan, Russian Federation

    L. Z. Latypova, G. A. Chmutova & A. R. Kurbangalieva

  2. A. E. Arbuzov Institute of Organic and Physical Chemistry, Federal Research Center “Kazan Scientific Center of the Russian Academy of Sciences”, 8 ul. Akad. Arbuzova, 420088, Kazan, Russian Federation

    V. V. Yanilkin

Authors
  1. L. Z. Latypova
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. G. A. Chmutova
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. A. R. Kurbangalieva
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. V. V. Yanilkin
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to L. Z. Latypova.

Additional information

Dedicated to Academician of the Russian Academy of Sciences A. I. Konovalov on the occasion of his 85th birthday.

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 2, pp. 0313–0327, February, 2019.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Latypova, L.Z., Chmutova, G.A., Kurbangalieva, A.R. et al. Mechanism of electrochemical reduction of 5-thio derivatives of 2(5H)-furanone. Russ Chem Bull 68, 313–327 (2019). https://doi.org/10.1007/s11172-019-2387-5

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11172-019-2387-5

Key words

Search

Navigation