STEPWISE OPENING OF CYCLIC SUBSTITUENTS OF BIS(OXONIUM) DERIVATIVES OF IRON(II) BIS(DICARBOLLIDE) BY PYRIDINE

Cover Page

Cite item

Full Text

Open Access Open Access
Restricted Access Access granted
Restricted Access Subscription or Fee Access

Abstract

The reaction of bis(dioxane) and bis(tetrahydropyran) derivatives of iron(II) bis(dicarbollide) [8,8'-{О(СН2СН2)2X}2-3,3'-Fe(1,2-C2B9H10)2] (X = О, СН2) with pyridine in an inert atmosphere has been studied. It was found that the ring-opening of oxonium cycles proceeds stepwise, with the formation of the corresponding mono- and dipyridinium iron(II) complexes. Using the bis(dioxane) dipyridinium derivative as an example, it was found that, when in solution, oxidation of the resulting products to the corresponding paramagnetic complexes of iron(III) is possible. This approach opens the way to obtain bifunctional iron bis(dicarbolide) derivatives with different substituents. The obtained compounds were characterized by multinuclear NMR and IR spectroscopy, as well as high-resolution mass spectrometry. The structure of the symmetrical dipyridinium iron(II) complex [8,8'-{С5H5NCH2CH2OCH2CH2O}2-3,3'-Fe(1,2-C2B9H10)2] was determined by single crystal X-ray diffraction.

About the authors

E. V Bogdanova

A.N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences

Email: bogdanovakatie@mail.ru
Moscow, Russia

K. E Erdelyi

A.N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences; National Research University "Higher School of Economics" (HSE University)

Email: bogdanovakatie@mail.ru

Faculty of Chemistry

Moscow, Russia

S. A Anufriev

A.N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences

Email: bogdanovakatie@mail.ru
Moscow, Russia

K. Yu Suponitsky

A.N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences

Email: bogdanovakatie@mail.ru
Moscow, Russia

M. Yu Stogniy

A.N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences

Email: bogdanovakatie@mail.ru
Moscow, Russia

I. B Sivaev

A.N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences

Author for correspondence.
Email: bogdanovakatie@mail.ru
Moscow, Russia

References

  1. Semioshkin A.A., Sivaev I.B., Bregadze V.I. // Dalton Trans. 2008. № 8. P. 977. https://doi.org/10.1039/B715363E.
  2. Sivaev I.B., Bregadze V.I. Boron Science. New Technologies and Applications / Ed. Hosmane N.S. Boca Raton: CRC Press, 2012. P. 623. https://doi.org/10.1201/b11199
  3. Друзина А.А., Шмалько А.В., Сисаев Н.Б., Брегадзе В.Н. // Успехи химии. 2021. Т. 90. № 7. C. 785.
  4. Ласькова Ю.Н., Серьохов А.А., Сиаев Н.Б. // Журн. неорган. химии. 2023. Т. 68. № 6. C. 701. https://doi.org/10.31857/S0044457X23600020
  5. Эрфел К.Э., Антонен А.А., Хидкова О.Б. и др. // Изв. Акад. наук. Сер. хим. 2023. № 4. C. 1059.
  6. Матвеев Е.Ю., Гараев Т.М., Новиков С.С. и др. // Журн. неорган. химии. 2023. Т. 68. № 6. C. 752. https://doi.org/10.31857/S0044457X22602413
  7. Матвеев Е.Ю., Кубасов А.С., Ничуговский А.И. и др. // Журн. неорган. химии. 2023. Т. 68. № 6. C. 724. https://doi.org/10.31857/S0044457X22602243
  8. Matveev E.Yu., Avdeeva V.V., Kubasov A.S. et al. // Inorganics. 2023. V. 11. № 4. P. 144. https://doi.org/10.3390/inorganics11040144
  9. Druzina A.A., Dudarova N.V., Ananyev I.V. et al. // Molecules. 2023. V. 28. № 18. P. 6636. https://doi.org/10.3390/molecules28186636
  10. Друзина А.А., Дударова Н.В., Сиаев Н.Б., Брегадзе В.Н. // Изв. Акад. наук. Сер. хим. 2023. № 9. C. 2083.
  11. Matveev E.Yu., Dorisova O.S., Avdeeva V.V. et al. // Molecules. 2023. V. 28. № 24. P. 8073. https://doi.org/10.3390/molecules28248073
  12. Okada S., Nishimura K., Alnaya Q. et al. // Mol. Pharmaceutics. 2023. V. 20. № 12. P. 6311. https://doi.org/10.1021/acs.molpharmaceut.3c00726
  13. Garvey T.M., Yadin I.I., Breslav N.V. et al. // Molecules. 2024. V. 29. № 24. P. 5886. https://doi.org/10.3390/molecules29245886
  14. Репинов В.М., Матвеев Е.Ю., Лисовский М.В. и др. // Изв. Акад. наук. Сер. хим. 2010. № 3. C. 538.
  15. Матвеев Е.Ю., Кубасов А.С., Разгоняева Г.А. и др. // Журн. неорган. химии. 2015. Т. 60. № 7. C. 858. https://doi.org/10.7868/S0044457X15070107
  16. Stogniy M.Yu., Anufriev S.A., Bogdanova E.V. et al. // Dalton Trans. 2024. V. 53. № 7. P. 3363. https://doi.org/10.1039/D3DT03549B
  17. APEX2 and SAINT; Bruker AXS Inc.: Madison, WI, USA, 2014.
  18. Sheldrick G.M. // Acta Crystallogr., Sect. C. 2015. V. 71. № 1. P. 3. https://doi.org/10.1107/S2053229614024218
  19. Semioshkin A., Nizhnik E., Godovikov I. et al. // J. Organomet. Chem. 2007. V. 692. № 19. P. 4020. https://doi.org/10.1016/j.jorganchem.2007.06.001
  20. Sivaev I.B., Starikova Z.A., Sjöberg S., Bregadze V.I. // J. Organomet. Chem. 2002. V. 649. № 1. P. 1. https://doi.org/10.1016/S0022-328X(01)01352-3
  21. Plések J., Grüner B., Macháček J. et al. // J. Organomet. Chem. 2007. V. 692. № 22. P. 4801. https://doi.org/10.1016/j.jorganchem.2007.07.026
  22. Hao E., Vicente M.G.H. // Chem. Commun. 2005. № 10. P. 1306. https://doi.org/10.1039/B415649H
  23. Hao E., Jensen T.J., Courtney B.H., Vicente M.G.H. // Bioconjugate Chem. 2005. V. 16. № 6. P. 1495. https://doi.org/10.1021/bc0502098
  24. Hussain S., Dong H., Zeng S. et al. // J. Mol. Liq. 2021. V. 336. P. 116362. https://doi.org/10.1016/j.molliq.2021.116362
  25. Anufriev S.A., Erokhina S.A., Supontisky K.Yu. et al. // J. Organomet. Chem. 2018. V. 865. P. 239. https://doi.org/10.1016/j.jorganchem.2018.04.019
  26. Anufriev S.A., Sivaev I.B., Supontisky K.Yu., Bregadze V.I. // J. Organomet. Chem. 2017. V. 849–850. P. 315. https://doi.org/10.1016/j.jorganchem.2017.03.025
  27. Anufriev S.A., Erokhina S.A., Supontisky K.Yu. et al. // Eur. J. Inorg. Chem. 2017. V. 2017. № 38–39. P. 4444. https://doi.org/10.1002/ejic.201700575

Supplementary files

Supplementary Files
Action
1. JATS XML
Download

Copyright (c) 2025 Russian Academy of Sciences