CATALYTIC SULFOXIDATION REACTIONS OF 1,3-BIS(PARA-TOLYL SULFIDE)-5-TERT-BUTYLBENZENE USING DECAVANADATE DERIVATIVES: Dedicated to Professor Luminița Silaghi-Dumitrescu on the Occasion of Her 75th Anniversary

Henrietta ALBERT-NAGY; Ioana SUCIU; Szidonia LAZSADI-RACZ; Meryem IDBOUMLIK; Mohammed LACHKAR; Gabriela NEMEȘ; Noemi DEAK

doi:10.24193/subbchem.2026.1.01

CATALYTIC SULFOXIDATION REACTIONS OF 1,3-BIS(PARA-TOLYL SULFIDE)-5-TERT-BUTYLBENZENE USING DECAVANADATE DERIVATIVES

Dedicated to Professor Luminița Silaghi-Dumitrescu on the Occasion of Her 75th Anniversary

Authors

Henrietta ALBERT-NAGY Babeş-Bolyai University, Faculty of Chemistry and Chemical Engineering, Doctoral School of Chemistry, Cluj-Napoca 400028, Romania
Ioana SUCIU Babeş-Bolyai University, Faculty of Chemistry and Chemical Engineering, Doctoral School of Chemistry, Cluj-Napoca 400028, Romania https://orcid.org/0009-0004-6437-6047
Szidonia LAZSADI-RACZ Babeş-Bolyai University, Faculty of Chemistry and Chemical Engineering, 11 Arany Janos str., RO-400028, Cluj-Napoca, Romania
Meryem IDBOUMLIK Babeş-Bolyai University, Faculty of Chemistry and Chemical Engineering, 11 Arany Janos str., RO-400028, Cluj-Napoca, Romania; Sidi Mohamed Ben Abdellah University, Faculty of Sciences, Engineering Laboratory of Organometallic, Molecular Materials, and Environment (LIMOME), Po. Box 1796 (Atlas), 30000, Fez, Morocco
Mohammed LACHKAR Sidi Mohamed Ben Abdellah University, Faculty of Sciences, Engineering Laboratory of Organometallic, Molecular Materials, and Environment (LIMOME), Po. Box 1796 (Atlas), 30000, Fez, Morocco https://orcid.org/0000-0002-6358-5363
Gabriela NEMEȘ Babeş-Bolyai University, Faculty of Chemistry and Chemical Engineering, 11 Arany Janos str., RO-400028, Cluj-Napoca, Romania https://orcid.org/0000-0003-4031-594X
Noemi DEAK Babeş-Bolyai University, Faculty of Chemistry and Chemical Engineering, 11 Arany Janos str., RO-400028, Cluj-Napoca, Romania. *Corresponding authors: noemi.deak@ubbcluj.ro, gabriela.nemes@ubbcluj.ro https://orcid.org/0000-0002-9401-0298

DOI:

https://doi.org/10.24193/subbchem.2026.1.01

Keywords:

catalytic sulfoxidation, bis-thioether, sulfide oxidation, green chemistry

Abstract

Catalytic sulfoxidation of 1,3-bis(para-tolyl sulfide)-5-tert-butylbenzene in order to obtain sulfones and sulfoxides, was carried out using three decavanadate (V₁₀O₂₈)^6- containing catalysts. Reaction conditions were varied to evaluate different parameters of the process; the tested procedures followed the guidelines of green chemistry. To align with these principles, reaction parameters were optimized at room temperature using environmentally benign solvents, including methanol, ethanol, iso-propanol, water, and ethylene glycol, as well as their mixtures with toluene. In this study we present a fast and environmentally friendly procedure to obtain sulfonyl and sulfinyl containing compounds through sulfoxidation of bis-thioether 1,3-bis(para-tolyl sulfide)-5-tert-butylbenzene.

References

1. M. Wang, X. Jiang, ACS Sustainable Chem. Eng. 2022, 10(2), 671–677.

2. S. Liang, K. Hofman, M. Friedrich, J. Keller, G. Manolikakes, ChemSusChem 2021, 14, 4878 – 4902.

3. J. Priego, O. García Mancheño, S. Cabrera, J. C. Carretero, J. Org. Chem. 2002, 67(4), 1346–1353.

4. G. Sipos, E. E. Drinkel, R. Dorta, Chem. Soc. Rev. 2015, 44, 3834– 3860.

5. B. M. Trost, M. Rao, Angew. Chem., Int. Ed. 2015, 54, 5026– 5043.

6. E. A. Ilardi, E. Vitaku, J. T. Njardarson, J. Med. Chem. 2014, 57(7), 2832–2842.

7. X. Chen, H. Wu, C.-M. Park, T. H. Poole, G. Keceli, N. O. Devarie-Baez, A.W.Tsang, W. T. Lowther, L. B. Poole, S. B. King, M. Xian, C. M. Furdui, ACS Chem. Biol. 2017, 12 (8), 2201–2208.

8. H. Mutlu, E. B. Ceper, X. Li, J. Yang, W. Dong, M. M. Ozmen, P. Theato, Macromol. Rapid Commun. 2018, 1800650.

9. S. Patai, Z. Rappoport, C. J. M. Stirling, The Chemistry of Sulphones and Sulphoxides, Wiley, New York, 1988.

10. E. Wojaczynska, J. Wojaczynski, Chem. Rev., 2010, 110, 4303–4356.

11. J.-E. Bäckvall, Modern Oxidation Methods, Wiley-VCH, Weinheim, 2004.

12. E. Wojaczyńska, J. Wojaczyński, Chem. Rev. 2020, 120(10), 4578–4611.

13. X. B. Liu, Q. Rong, J. Tan, C. Chen, Y. L. Hu, Front. Chem. 2022, 9, 798603.

14. J.-P. Cao, Y.-S. Xue, N.-F. Li, J.-J. Gong, R.-K. Kang, Y. Xu, J. Am. Chem. Soc. 2019, 141(49), 19487–19497.

15. W. Al-Maksoud, S. Daniele, A.B. Sorokin, Green Chem., 2008, 10, 447–451.

16. F. Rajabi, E. Vessally, R. Luque R, L. Voskressensky, Molecular Catalysis, 2021, 515, 111931.

17. N. Deak, D.Madec, G. Nemes, Eur. J. Inorg. Chem, 2020, 2769-2790.

18. N. Deak, O. Thillaye du Boullay, S. Mallet-Ladeira, I.-T. Moraru, D. Madec, G.Nemes, Eur. J. Inorg. Chem, 2020, 3729-3737.

19. N. Deak, P. M. Petrar, S. Mallet-Ladeira, L. Silaghi-Dumitrescu, G. Nemeş, D.Madec, Chem. Eur. J., 2016, 22, 1349-1354.

20. N. Deak, O. Thillaye du Boullay, I.-T. Moraru, S. Mallet-Ladeira, D.Madec, G.Nemes, Dalton Trans., 2019, 48, 2399-2406.

21. N. Deak, R. Septelean, I.-T. Moraru, S. Mallet-Ladeira, D. Madec, G. Nemes, Studia UBB Chemia, 2018, LXIII (2), 105-115

22. N. Deak, M. Idboumlik, A. Soran, M. Lachkar, B. El Bali, G. Nemes; Stud. Univ. Babes-Bolyai, Chem., 2024, 69, 7–23.

23. M. Idboumlik, M. Kadiri, N. Hamdi, M. Driouch, A.F.I. Ngopoh, I. Lakkab, E-E. Bendeif, M. Sfaira, B. El Bali, M. Lachkar, A. Zarrouk, Mater. Chem. Phys., 2022, 287, article no. 126211.

24. M. Idboumlik, I. Lakkab, S. Erraouan, N. Hamdi, M. Lachkar, M. Dusek, V. Eigner, B. El Bali, J. Mol. Struct., 2024, 1312, article no. 138551.

25. P. T. Anastas and J. C. Warner, Green Chemistry: Theory and Practice, Oxford University Press, 1998.

26. A.M. Afanasenko, N. Deak, J. October, R. Sole, K. Barta, Green Chem., 2025, 27, 5947-5981.

27. D. Prat, A. Wells, J. Hayler, H. Sneddon, C.R. McElroy, S. Abou-Shehadad, P.J.Dunn, Green Chem., 2016,18, 288-296.

28. D. Prat, J. Hayler, A. Wells, Green Chem., 2014, 16, 4546-4551.

STUDIA UBB CHEMIA, Volume 71 (LXXI), No. 1, March 2026

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Published

2026-03-25

How to Cite

ALBERT-NAGY, H., SUCIU, I., LAZSADI-RACZ, S., IDBOUMLIK, M., LACHKAR, M., NEMEȘ, G., & DEAK, N. (2026). CATALYTIC SULFOXIDATION REACTIONS OF 1,3-BIS(PARA-TOLYL SULFIDE)-5-TERT-BUTYLBENZENE USING DECAVANADATE DERIVATIVES: Dedicated to Professor Luminița Silaghi-Dumitrescu on the Occasion of Her 75th Anniversary. Studia Universitatis Babeș-Bolyai Chemia, 71(1), 7–18. https://doi.org/10.24193/subbchem.2026.1.01