Skip to main content
Log in

Aluminum hydrogen sulfate [Al(HSO4)3] as an efficient catalyst for the preparation of thioacetals

  • Published:
Research on Chemical Intermediates Aims and scope Submit manuscript

Abstract

Aluminum hydrogen sulfate, as a heterogeneous solid acid catalyst, has been used for the mild conversion of carbonyl compounds to their thioacetals using 1,2- and 1,3-dithiol under ambient conditions with short reaction times in high to excellent yield in acetonitrile as solvent.

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.

Institutional subscriptions

Scheme 1
Scheme 2
Fig. 1

Similar content being viewed by others

References

  1. T.W. Greene, P.G.M. Wuts, Protective Groups in Organic Synthesis, 3rd edn. (Wiley, New York, 1999)

    Book  Google Scholar 

  2. E.J. Corey, D. Seebach, J. Org. Chem. 31, 4097 (1966)

    Article  CAS  Google Scholar 

  3. D. Seebach, Angew. Chem. Int. Ed. Engl. 8, 639 (1969)

    Article  CAS  Google Scholar 

  4. B.T. Grobel, D. Seebach, Synthesis 357 (1977)

  5. P.C. Bulman-Page, M.B. Van-Niel, J.C. Prodger, Tetrahedron 45, 7643 (1989)

    Article  Google Scholar 

  6. Thioacetals are commonly prepared by the condensation of carbonyl compounds with thiols or dithiols. For the review, please see references 6–39: S.K. De, Adv. Synth. Catal. 347, 673 (2005)

  7. G. Sartori, R. Ballini, F. Bigi, G. Bosica, R. Maggi, P. Righi, Chem. Rev. 104, 199 (2004)

    Article  CAS  Google Scholar 

  8. J.S. Yadav, B.V.S. Reddy, S.K. Pandey, Synlett 238 (2001)

  9. A. Kamal, G. Chouhan, Tetrahedron Lett. 43, 1347 (2002)

    Article  CAS  Google Scholar 

  10. S. Muthusamy, S.A. Babu, C. Gunanathan, Tetrahedron Lett. 42, 359 (2001)

    Article  CAS  Google Scholar 

  11. B. Burczyk, Z. Kortylewticz, Synthesis 831 (1982)

  12. Y. Kamitori, M. Hojo, R. Masuda, T. Kimura, T. Yoshida, J. Org. Chem. 51, 1427 (1986)

    Article  CAS  Google Scholar 

  13. B. Tamami, K.P. Borujeny, Synth. Commun. 33, 4253 (2003)

    Article  CAS  Google Scholar 

  14. B. Das, R. Ramu, M.R. Reddy, G. Machender, Synthesis 250 (2005)

  15. S. Rudrawar, R.C. Besra, A.K. Chakraborti, Synthesis 2767 (2006)

  16. M.H. Ali, M.G. Gomes, Synthesis 1326 (2005)

  17. A.T. Khan, E. Mondal, P.R. Sahu, S. Islam, Tetrahedron Lett. 44, 919 (2003)

    Article  CAS  Google Scholar 

  18. N. Srivastava, S.K. Dashgupta, B.K. Banik, Tetrahedron Lett. 44, 1191 (2003)

    Article  CAS  Google Scholar 

  19. N.M. Leonard, M.C. Oswald, D.A. Friederg, B.A. Nattier, R.C. Smith, R.S. Mohan, J. Org. Chem. 67, 5202 (2002)

    Article  CAS  Google Scholar 

  20. S.K. De, Tetrahedron Lett. 45, 2339 (2004)

    Article  CAS  Google Scholar 

  21. H. Adibi, H. Samimi, N. Iranpoor, Chin. J. Chem. 26, 2086 (2008)

    Article  CAS  Google Scholar 

  22. H. Veisi, M. Amiri, A.H. Hamidian, J. Malakootikhah, L. Fatolahi, A. Faraji, A. Sedrpoushan, B. Maleki, S. Ghahri Saremi, M. Noroozi, F. Bahadoori, S. Veisi, Phosphorus Sulfur Silicon Relat. Elem. 185, 689 (2010)

    Article  CAS  Google Scholar 

  23. A.R. Hajipour, P. Hosseini, A.E. Ruoho, Phosphorus Sulfur Silicon Relat. Elem. 183, 2502 (2008)

    Article  CAS  Google Scholar 

  24. H.R. Shaterian, H.R. Ahmadian, M. Ghashang, R. Doostmohammadi, H. Yarahmadi, Phosphorus Sulfur Silicon Relat. Elem. 183, 1099 (2008)

    Article  CAS  Google Scholar 

  25. H.R. Shaterian, A. Hosseinian, M. Ghashang, F. Khorami, Phosphorus Sulfur Silicon Relat. Elem. 183, 2490 (2008)

    Article  CAS  Google Scholar 

  26. A.R. Hajipour, A. Zarei, L. Khazdooz, S. Zahmatkesh, A.E. Ruoho, Phosphorus Sulfur Silicon Relat. Elem. 181, 387 (2006)

    Article  CAS  Google Scholar 

  27. H. Firouzabadi, N. Iranpoor, H. Hazarkhani, Phosphorus Sulfur Silicon Relat. Elem. 177, 2571 (2002)

    Article  CAS  Google Scholar 

  28. F. Matloubi Moghaddam, G. Rezanejade Bardajee, A. Arefi Oskui, Phosphorus Sulfur Silicon Relat. Elem. 181, 1445 (2006)

    Article  Google Scholar 

  29. S.A. Pourmousavi, M. Hadavandkhani, J. Sulfur Chem. 30, 37 (2009)

    Article  Google Scholar 

  30. K. Bahrami, M.M. Khodaei, M. Tajik, M. Soheilizad, J. Sulfur Chem. 32, 397 (2011)

    Article  CAS  Google Scholar 

  31. M. Srinivasulu, K. Rajesh, N. Suryakiran, J. Jon Paul Selvam, Y. Venkateswarlu, J. Sulfur Chem. 28, 245 (2007)

    Article  CAS  Google Scholar 

  32. B. Karami, M. Taei, S. Khodabakhshi, M. Jamshidi, J. Sulfur Chem. 33, 65 (2012)

    Article  CAS  Google Scholar 

  33. For the preparation of Al(HSO4)3 please see references 33–38: F. Shirini, M.A. Zolfigol, P. Salehi, M. Abedini, Curr. Org. Chem. 12, 183 (2008)

    Google Scholar 

  34. K. Niknam, M.A. Zolfigol, M. Shayegh, R. Zare, J. Chin. Chem. Soc. 54, 1067 (2007)

    CAS  Google Scholar 

  35. F. Shirini, M.A. Zolfigol, M. Abedini, Bull. Chem. Soc. Jpn. 78, 1982 (2005)

    Article  CAS  Google Scholar 

  36. B.F. Mirjalili, M.A. Zolfigol, A. Bamoniri, M.A. Amrollahi, N. Sheikhan, Russ. J. Org. Chem. 43, 852 (2007)

    Article  CAS  Google Scholar 

  37. F. Shirini, M.A. Zolfigol, M. Abedini, P. Salehi, Bull. Korean Chem. Soc. 24, 1683 (2003)

    Article  CAS  Google Scholar 

  38. K. Niknam, M.A. Zolfigol, T. Sadabadi, A. Nejati, J. Iran. Chem. Soc. 3, 318 (2006)

    Article  CAS  Google Scholar 

Download references

Acknowledgment

The authors are indebted to the Islamic Azad University, Najafabad Branch for financial support of this research.

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Majid Ghashang.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Ghashang, M. Aluminum hydrogen sulfate [Al(HSO4)3] as an efficient catalyst for the preparation of thioacetals. Res Chem Intermed 39, 2837–2842 (2013). https://doi.org/10.1007/s11164-012-0802-8

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11164-012-0802-8

Keywords

Navigation