Skip to main content
Log in

Synthesis of New Iminium Derivatives of Sulphonio-сloso-Decaborate Anion (Bu4N)[2-B10H9SC(NH2)R] (R = –CH3, –CH2CH3, –CH(CH3)2, –Ph, –PhCH3)

  • COORDINATION COMPOUNDS
  • Published:
Russian Journal of Inorganic Chemistry Aims and scope Submit manuscript

Abstract

New iminium derivatives of the sulfonio-closo-decaborate anion have been obtained in the form of tetrabutylammonium salts (Bu4N)[2-B10H9SC(NH2)R] (R = –CH3, –CH2CH3, –CH(CH3)2, –Ph, –PhCH3), in which the iminium group acts as a protective group and allows further modification of the boron cluster anion without acting the sulfonium group. The compounds have been studied by elemental analysis, IR and 11B, 1H, 13C NMR spectroscopies. The structure of compounds (Bu4N)[2-B10H9SC(NH2)CH3] and (Bu4N)[2-B10H9SC(NH2)Ph] has been confirmed by X-ray diffraction analysis. The yield of final compounds is >80%.

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.

Fig. 1.
Fig. 2.
Fig. 3.
Fig. 4.
Fig. 5.

Similar content being viewed by others

REFERENCES

  1. B. P. Dash, R. Satapathy, J. A. Maguire, et al., New J. Chem. 35, 1955 (2011). https://doi.org/10.1039/c1nj20228f

    Article  CAS  Google Scholar 

  2. J. C. Axtell, L. M. A. Saleh, E. A. Qian, et al., Inorg. Chem. 57, 2333 (2018). https://doi.org/10.1021/acs.inorgchem.7b02912

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  3. M. Y. Stogniy, E. V. Bogdanova, S. A. Anufriev, et al., Russ. J. Inorg. Chem. 67, 1537 (2022). https://doi.org/10.1134/S0036023622600848

    Article  CAS  Google Scholar 

  4. B. P. Dash, R. Satapathy, E. R. Gaillard, et al., J. Am. Chem. Soc. 132, 6578 (2010). https://doi.org/10.1021/ja101845m

    Article  CAS  PubMed  Google Scholar 

  5. Y. S. Bae, A. M. Spokoyny, O. K. Farha, et al., Chem. Commun. 46, 3478 (2010). https://doi.org/10.1039/b927499e

    Article  CAS  Google Scholar 

  6. S. Gao, Y. Zhu, and N. Hosmane, Boron-Based Compd. Potential Emerg. Appl. Med. 371 (2018). https://doi.org/10.1002/9781119275602.ch3.4

  7. A. Jankowiak, J. Kanazawa, P. Kaszynski, et al., J. Organomet. Chem. 747, 195 (2013). https://doi.org/10.1016/j.jorganchem.2013.05.034

    Article  CAS  Google Scholar 

  8. K. Goossens, K. Lava, C. W. Bielawski, et al., Chem. Rev. 116, 4643 (2016). https://doi.org/10.1021/cr400334b

    Article  CAS  PubMed  Google Scholar 

  9. F. Ali, N. Hosmane, and Y. Zhu, Molecules 25, 828 (2020). https://doi.org/10.3390/molecules25040828

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  10. E. Yu. Matveev, T. M. Garaev, S. S. Novikov, et al., Russ. J. Inorg. Chem. 68, 670 (2023). https://doi.org/10.1134/S0036023623600533

    Article  CAS  Google Scholar 

  11. I. B. Sivaev, A. V. Prikaznov, and D. Naoufal, Collect. Czech. Chem. Commun. 75, 1149 (2010). https://doi.org/10.1135/cccc2010054

    Article  CAS  Google Scholar 

  12. A. V. Nelyubin, I. N. Klyukin, N. A. Selivanov, et al., Russ. J. Inorg. Chem. 68, 658 (2023). https://doi.org/10.1134/S003602362360048X

    Article  Google Scholar 

  13. V. V. Voinova, I. N. Klyukin, A. S. Novikov, et al., Russ. J. Inorg. Chem. 66, 295 (2021). https://doi.org/10.1134/S0036023621030190

    Article  CAS  Google Scholar 

  14. E. Yu. Matveev, V. M. Retivov, G. A. Razgonyaeva, et al., Russ. J. Inorg. Chem. 56, 1549 (2011). https://doi.org/10.1134/S0036023611100160

    Article  CAS  Google Scholar 

  15. A. S. Kubasov, E. S. Turishev, A. V. Golubev, et al., Inorg. Chim. Acta 507 (2020). https://doi.org/10.1016/j.ica.2020.119589

  16. A. L. Mindich, N. A. Bokach, M. L. Kuznetsov, et al., ChemPlusChem 77, 1075 (2012). https://doi.org/10.1002/cplu.201200257

    Article  CAS  Google Scholar 

  17. N. K. Neumolotov, N. A. Selivanov, A. Yu. Bykov, et al., Russ. J. Inorg. Chem. 67, 1583 (2022). https://doi.org/10.1134/S0036023622600861

    Article  CAS  Google Scholar 

  18. S. V. Ivanov, S. M. Miller, O. P. Anderson, et al., J. Am. Chem. Soc. 125, 4694 (2003). https://doi.org/10.1021/ja0296374

    Article  CAS  PubMed  Google Scholar 

  19. C. Bolli, J. Derendorf, C. Jenne, et al., Eur. J. Inorg. Chem. 2017, 4552 (2017). https://doi.org/10.1002/ejic.201700620

    Article  CAS  Google Scholar 

  20. J. Warneke, S. Z. Konieczka, G. L. Hou, et al., Phys. Chem. Chem. Phys. 21, 5903 (2019). https://doi.org/10.1039/c8cp05313h

    Article  CAS  PubMed  Google Scholar 

  21. A. Jankowiak, A. Balinski, J. E. Harvey, et al., J. Mater. Chem. 1, 1144 (2013). https://doi.org/10.1039/c2tc00547f

    Article  CAS  Google Scholar 

  22. P. Kaszyński and B. Ringstrand, Angew. Chem., Int. Ed. Engl. 54, 6576 (2015). https://doi.org/10.1002/anie.201411858

    Article  CAS  PubMed  Google Scholar 

  23. V. V. Voinova, N. A. Selivanov, A. Yu. Bykov, et al., Russ. J. Inorg. Chem. 68, 678 (2023). https://doi.org/10.1134/S003602362360017X

    Article  CAS  Google Scholar 

  24. M. Schelhaas and H. Waldmann, Angew. Chem., Int. Ed. Engl. 35, 2056 (1996). https://doi.org/10.1002/anie.199620561

    Article  CAS  Google Scholar 

  25. M. Bols and C. M. Pedersen, Beilstein J. Org. Chem. 13, 93 (2017). https://doi.org/10.3762/bjoc.13.12

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  26. J. S. Davies, C. L. Higginbotham, E. J. Tremeer, et al., J. Chem. Soc., Perkin Trans. 22, 3043 (1992). https://doi.org/10.1039/p19920003043

    Article  Google Scholar 

  27. E. M. Dangerfield, C. H. Plunkett, A. L. Win-Mason, et al., Org. Chem. 75, 5470 (2010). https://doi.org/10.1021/jo100004c

    Article  CAS  Google Scholar 

  28. P. Y. Reddy, S. Kondo, and T. Toru, Org. Chem. 62, 2652 (1997). https://doi.org/10.1021/jo962202c

    Article  CAS  Google Scholar 

  29. B. Zeysing, C. Gosch, and A. Terfort, Org. Lett. 2, 1843 (2000). https://doi.org/10.1021/ol0058902

    Article  CAS  PubMed  Google Scholar 

  30. T. W. Greene and P. G. M. Wuts, in Protective Groups in Organic Synthesis (John Wiley, 1999). https://doi.org/10.1002/0471220574

    Book  Google Scholar 

  31. A. S. Kubasov, E. S. Turishev, I. N. Polyakova, et al., J. Organomet. Chem. 828, 106 (2017). https://doi.org/10.1016/j.jorganchem.2016.11.035

    Article  CAS  Google Scholar 

  32. Bruker, SAINT, Bruker AXS Inc., Madison (WI), USA, 2018.

    Google Scholar 

  33. G. M. Sheldrick, Acta Crystallogr., Sect. C: Struct. Chem. 71, 3 (2015). https://doi.org/10.1107/S2053229614024218

    Article  CAS  Google Scholar 

  34. L. Krause, R. Herbst-Irmer, G. M. Sheldrick, et al., J. Appl. Crystallogr. 48, 3 (2015). https://doi.org/10.1107/S1600576714022985

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  35. O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, et al., J. Appl. Crystallogr. 42, 339 (2009). https://doi.org/10.1107/S0021889808042726

    Article  CAS  Google Scholar 

  36. P. R. Spackman, M. J. Turner, J. J. McKinnon, et al., J. Appl. Crystallogr. 54, 1006 (2021). https://doi.org/10.1107/S1600576721002910

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  37. A. S. Kubasov, A. V. Golubev, A. Y. Bykov, et al., J. Mol. Struct. 1241, 130591 (2021). https://doi.org/10.1016/j.molstruc.2021.130591

    Article  CAS  Google Scholar 

  38. M. O. Ali, J. C. Lasseter, R. Żurawiński, et al., Chem.–A Eur. J. 25, 2616 (2019). https://doi.org/10.1002/chem.201805392

    Article  CAS  Google Scholar 

  39. R. G. Kultyshev, J. Liu, E. A. Meyers, et al., Inorg. Chem. 39, 3333 (2000). https://doi.org/10.1021/ic000198o

    Article  CAS  PubMed  Google Scholar 

  40. J. Axhausen, C. Ritter, K. Lux, et al., Z. Anorg. Allg. Chem. 639, 65 (2013). https://doi.org/10.1002/zaac.201200419

    Article  CAS  Google Scholar 

  41. H. C. Chang, Y. C. Hsu, C. H. Chen, et al., Dalton Trans. 44, 20808 (2015). https://doi.org/10.1039/c5dt03316k

    Article  CAS  PubMed  Google Scholar 

Download references

ACKNOWLEDGMENTS

Analytical studies (measurements of NMR spectra, X‑ray diffraction studies) were carried out at the Center for Collective Use of Physical Research Methods at the Kurnakov Institute of General and Inorganic Chemistry of the Russian Academy of Sciences.

Funding

The work was supported by the Russian Science Foundation (grant no. 23-73-00082).

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to A. V. Golubev.

Ethics declarations

The authors declare that they have no conflicts of interest.

Additional information

Translated by V. Avdeeva

Publisher’s Note.

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

Supplementary Information

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Golubev, A.V., Kubasov, A.S., Lukoshkova, A.A. et al. Synthesis of New Iminium Derivatives of Sulphonio-сloso-Decaborate Anion (Bu4N)[2-B10H9SC(NH2)R] (R = –CH3, –CH2CH3, –CH(CH3)2, –Ph, –PhCH3). Russ. J. Inorg. Chem. 68, 1752–1760 (2023). https://doi.org/10.1134/S0036023623602350

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S0036023623602350

Keywords:

Navigation