Skip to main content
Log in

Ultrasound-Assisted Synthesis of C60 Fullerene-Fused 1,4-Oxathian-2-ones

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

Abstract

Previously unknown C60 fullerene-fused 1,4-oxathian-2-ones 1,9-[2′-oxo-1′,4′-oxathiano]-1,9-dihydro-(C60-Ih)[5,6]fullerene and 1,9-[3′-Methyl-2′-oxo-1′,4′-oxathiano]-1,9-dihydro-(C60-Ih)[5,6]fullerene were obtained by a selective reaction mercaptocarboxylic acids (mercaptoacetic and 2-mercaptopropionic) with fullerene epoxide C60O in the presence of NaOH in an inert atmosphere at room temperature under ultrasonication for 1 h. The yields of the target product were estimated at 96 and 87%, respectively (by HPLC). A plausible reaction mechanism for was proposed.

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.

Scheme
Scheme

REFERENCES

  1. Nakamura, E. and Isobe, H., Acc. Chem. Res., 2003, vol. 36, p. 807. https://doi.org/10.1021/ar030027y

    Article  CAS  PubMed  Google Scholar 

  2. Tzirakis, M.D. and Orfanopoulos, M., Chem. Rev., 2013, vol. 113, p. 5262. https://doi.org/10.1021/cr300475r

    Article  CAS  PubMed  Google Scholar 

  3. Echegoyen, L. and Echegoyen, L.E., Acc. Chem. Res., 1998, vol. 31, p. 593. https://doi.org/10.1021/ar970138v

    Article  CAS  Google Scholar 

  4. Matsuo, Y., Chem. Lett., 2012, vol. 41, p. 754. https://doi.org/10.1246/cl.2012.754

    Article  CAS  Google Scholar 

  5. Dennler, G., Scharber, M.C., and Brabec, C.J., Adv. Mater., 2009, vol. 21, p. 1323. https://doi.org/10.1002/adma.200801283

    Article  CAS  Google Scholar 

  6. Miyauchi, H., Tanio, T., and Ohashi, N., Med. Chem. Lett., 1996, vol. 6, p. 2377. https://doi.org/10.1016/0960-894X(96)00435-0

    Article  CAS  Google Scholar 

  7. Singh, A.K., Rai, A., and Yadav, L.D.S., Tetrahedron Lett., 2011, vol. 52, p. 3614. https://doi.org/10.1016/j.tetlet.2011.05.010

    Article  CAS  Google Scholar 

  8. Kinzyabaeva, Z.S. and Sharipov, G.L., Ultrason. Sonochem., 2020, vol. 67, p. 105169. https://doi.org/10.1016/j.ultsonch.2020.105169

    Article  CAS  PubMed  Google Scholar 

  9. Kaufmann, H.P. and Schickel, R., Fette Seifen Anstrichm., 1963, vol. 65, p. 851. https://doi.org/10.1002/lipi.19630651017

    Article  CAS  Google Scholar 

  10. Black, D.K., J. Chem. Soc. C, 1966, p. 1708. https://doi.org/10.1039/J39660001708

  11. Orszulik, S.T., Tetrahedron Lett., 1986, vol. 27, p. 3781. https://doi.org/10.1016/S0040-4039(00)83879-4

    Article  Google Scholar 

  12. Morgunova, V.A., Nikitina, L.E., Piemenkov, V.V., Fazlyeva, M.G., and Chugunov, Yu.V., Chem. Nat. Compd., 1999, vol. 35, p. 176. https://doi.org/10.1007/BF02234928

    Article  CAS  Google Scholar 

  13. O’Sullivan, O.C.M., Collins, S.G., Maguire, A.R., Bohm, M., and Sander, W., Eur. J. Org. Chem., 2006, vol. 13, p. 2918. https://doi.org/10.1002/ejoc.200500971

    Article  CAS  Google Scholar 

  14. Mandrus, D., Kele, M., Hettich, R.L., Guiochon, G., Sales, B.C., and Boatner, L.A., J. Phys. Chem. B, 1997, vol. 101, p. 123. https://doi.org/10.1021/jp962056e

    Article  CAS  Google Scholar 

  15. Ko, W.B., Nam, J.H., and Hwang, S.H., Ultrasonics, 2004, vol. 42, p. 611. https://doi.org/10.1016/j.ultras.2004.01.083

    Article  CAS  PubMed  Google Scholar 

  16. Zhang, X., Gan, L., Huang, S., and Shi, Y., J. Org. Chem., 2004, vol. 69, p. 5800. https://doi.org/10.1021/jo0493368

    Article  CAS  PubMed  Google Scholar 

  17. Safaei-Ghomi, J. and Masoomi, R., Ultrason. Sonochem., 2015, vol. 23, p. 212. https://doi.org/10.1016/j.ultsonch.2014.08.004

    Article  CAS  PubMed  Google Scholar 

  18. Yinghuai, Z., Bahnmueller, S., Chibun, C., Carpenter, K., Hosmane, N.S., and Maguirec, J.A., Tetrahedron Lett., 2003, vol. 44, p. 5473. https://doi.org/10.1016/S0040-4039(03)01299-1

    Article  CAS  Google Scholar 

  19. Yinghuai, Z., J. Phys. Chem. Solids, 2004, vol. 65, p. 349. https://doi.org/10.1016/j.jpcs.2003.08.027

    Article  CAS  Google Scholar 

  20. Cataldo, F., Ursini, O., and Ragni, P., Plasma Chem. Plasma Process, 2013, vol. 33, p. 355. https://doi.org/10.1007/s11090-012-9417-5

    Article  CAS  Google Scholar 

  21. Cataldo, F., Garcia-Hernandez, D.A., and Manchado, A., Fullerene Nanotube Carbon Nanostruct., 2014, vol. 22, p. 565. https://doi.org/10.1080/1536383X.2012.702160

    Article  CAS  Google Scholar 

  22. Yoon, S., Hwang, S.H., and Ko, W.B., Curr. App. Phys., 2008, vol. 8, p. 774. https://doi.org/10.1016/j.cap.2007.04.022

    Article  Google Scholar 

  23. Andrievsky, G.V., Kosevich, M.V., Vovk, O.M., Shelkovsky, V.S., and Vashchenko, L.A., J. Chem. Soc., Chem. Commun., 1995, p. 1281. https://doi.org/10.1039/C39950001281

  24. Ko, W.B., Heo, J.Y., Nam, J.H., and Lee, K.B., Ultrasonics, 2004, vol. 41, p. 727. https://doi.org/10.1016/j.ultras.2003.12.029

    Article  CAS  PubMed  Google Scholar 

  25. Afreen, S., Muthoosamy, K., and Manickam, S., Ultrason. Sonochem., 2019, vol. 51, p. 451. https://doi.org/10.1016/j.ultsonch.2018.07.015

    Article  CAS  PubMed  Google Scholar 

  26. Afreen, S., Kokubo, K., Muthoosamy, K., and Manickam, S., RSC Adv., 2017, vol. 7, p. 31930. https://doi.org/10.1039/c7ra03799f

    Article  CAS  Google Scholar 

  27. Kinzyabaeva, Z.S. and Sharipov, G.L., Ultrason. Sonochem., 2018, vol. 42, p. 119. https://doi.org/10.1016/j.ultsonch.2017.11.012

    Article  CAS  PubMed  Google Scholar 

  28. Sivakumar, M., Senthilkumar, P., Majumdar, S., and Pandit, A.B., Ultrason. Sonochem., 2002, vol. 9, p. 25. https://doi.org/10.1016/S1350-4177(01)00099-2

    Article  CAS  PubMed  Google Scholar 

  29. Manickam, S., Arigela, V.N.D., and Gogate, P.R., Fuel Proces. Technol., 2014, vol. 128, p. 388. https://doi.org/10.1016/j.fuproc.2014.08.002

    Article  CAS  Google Scholar 

  30. Bulgakov, R. G., Kinzyabaeva, Z.S., Khalilov, L.M., and Yanybin, V.M., Russ. J. Org. Chem., 2010, vol. 46, p. 1776. https://doi.org/10.1134/s107042801012002x

    Article  CAS  Google Scholar 

  31. Rabinovich, V.A. and Khavin, Z.Ya., Kratkii khimicheskii spravochnik (Concise Chemical Reference Book), Leningrad: Khimiya, 1991.

  32. Isaacs, L., Wehrsig, A., and Diederich, F., Helv. Chim. Acta, 1993, vol. 76, p. 1231. https://doi.org/10.1002/hlca.19930760310

    Article  CAS  Google Scholar 

  33. Elemes, Y., Silverman, S.K., Sheu, C., Kao, M., Foote, C.S., Alvarez, M.M., and Whetten, R.L., Angew. Chem. Int. Ed., 1992, vol. 31, p. 351. https://doi.org/10.1002/anie.199203511

    Article  Google Scholar 

  34. Hirsch, A., Synthesis, 1995, vol. 8, p. 895. https://doi.org/10.1055/s-1995-4046

    Article  Google Scholar 

  35. Kampe, K.-D., Egger, N., and Vogel, M., Аngew. Chem. Inr. Ed., 1993, vol. 32, p. 1174. https://doi.org/10.1002/anie.199311741

    Article  Google Scholar 

  36. Parker, E. and Isaacs, N.S., Chem. Rev., 1959, vol. 59, p. 737. https://doi.org/10.1021/cr50028a006

    Article  CAS  Google Scholar 

Download references

ACKNOWLEDGMENTS

The structural studies were conducted at the “Agidel” Center for Collective Use, Institute of Petrochemistry and Catalysis, Ufa Federal Research Center, Russian Academy of Sciences.

Funding

The work was funded by the Ministry for Education and Science of the Russian Federation in the framework of the State order (topic FMRS-2022-0077).

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Z. S. Kinzyabaeva.

Ethics declarations

The authors declare no conflict of interest.

Additional information

To the 85th Anniversary of B.A. Trofimov

Publisher's Note. Pleiades Publishing remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Kinzyabaeva, Z.S. Ultrasound-Assisted Synthesis of C60 Fullerene-Fused 1,4-Oxathian-2-ones. Russ J Gen Chem 93 (Suppl 1), S131–S136 (2023). https://doi.org/10.1134/S1070363223140219

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070363223140219

Keywords:

Navigation