Skip to main content
SpringerLink
Log in

Comparison of the efficiency of two dicationic ionic liquids catalysts based on perchloric acid for the protection of alcohols

  • Original Paper
  • Published:
Journal of the Iranian Chemical Society Aims and scope Submit manuscript

Abstract

In this article, two aliphatic and aromatic types of dicationic acidic ionic liquids formulated as [H2-DABCO][ClO4], [H2-Bisim][ClO4]2 were used for the acceleration of the protection of alcohols as their corresponding trimethylsilyl (TMS), tetrahydropyranyl (THP) and methoxymethyl (MOM) ethers and the achieved results were compared. The performance of the catalyst was equal. All reactions were performed under mild conditions with good to high yields during short reaction times. Although in most cases the performance of both of the catalysts is equal, but TMS protection in the presence of [H2-Bisim][ClO4]2 needed lower amounts of the catalyst.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Scheme 1
Scheme 2
Scheme 3
Scheme 4

Similar content being viewed by others

References

  1. I. Mohammdpoor -Baltork, H. Aliyan, A. R. Khosropour, Tetrahedron Lett. 57: 5851 (2001)

  2. T. Greene, P. Wuts, Green’s Protective Groups in Organic Synthesis, 2nd edn. (John Wiley, New York, 1991)

    Google Scholar 

  3. G. Satari, R. Balini, F. Bigi, G. Bosica, R. Maggi, P. Righi, Chem. Rev. 104, 199 (2004)

    Article  CAS  Google Scholar 

  4. F. Shirini, N.G. Khaligh, Phosphorus Sulfur Silicon Relat. Elem. 186, 2156 (2011)

    Article  CAS  Google Scholar 

  5. M. Moghadam, Sh. Tangestaninejad, V. Mirkhani, I. Mohammadpoor-Baltork, S. Gharaati, Appl. Organometal. Chem. 23, 446 (2009)

    Article  CAS  Google Scholar 

  6. F. Shirini, M. Mamaghani, S.V. Atghia, Appl. Clay Sci. 58, 67 (2012)

    Article  CAS  Google Scholar 

  7. F. Shirini, M. Esm-Hosseini, Z. Hejazi, Synth. Commun. 35, 2913 (2005)

    Article  CAS  Google Scholar 

  8. M. Moghadam, Sh. Tangestaninejad, V. Mirkhani, I. Mohammadpoor-Baltork, S. Gharaati, Polyhedron 29, 212 (2010)

    Article  CAS  Google Scholar 

  9. M.A. Zolfigol, S. Sajjadifar, A. Ghorbani-Choghamarani, F. Tami, Res. Chem. Intermediat. 44, 7093 (2018)

    Article  CAS  Google Scholar 

  10. B. Zeynizadeh, S. Sorkhabi, Phosphorus Sulfur Silicon Relat. Elem. 193, 127 (2018)

    Article  CAS  Google Scholar 

  11. L.C. Branco, C.A.M. Afanso, Tetrahedron Lett. 57, 4405 (2001)

    Article  CAS  Google Scholar 

  12. F. Shirini, M. Abedini, N. Mahmoodi, M. Biglari, M.S.N. Langrudi, Phosphorus Sulfur Silicon Relat. Elem. 190, 1912 (2015)

    Article  CAS  Google Scholar 

  13. S.R. Churipard, K.S. Kanakikodi, N. Jose, S.P. Maradur, ChemistrySelect 5, 293 (2020)

    Article  CAS  Google Scholar 

  14. K. Rajkumari, I.B. Laskar, A.B. Kalita, L. Rokhum, React. Funct. Polym. 149, 104519 (2020)

    Article  CAS  Google Scholar 

  15. S. Mahato, R. Chatterjee, N.C. Ghosal, A. Majee, Synth. Commun. 47, 1905 (2017)

    Article  CAS  Google Scholar 

  16. A.R. Hajipour, M. Kargosha, A.E. Ruoho, Synth. Commun. 39, 1084 (2009)

    Article  CAS  Google Scholar 

  17. F. Shirini, M. Abedini, A. Pourvali, Chin. Chem. Lett. 22, 33 (2011)

    Article  CAS  Google Scholar 

  18. M. Curini, F. Epifano, M.C. Marcotullio, O. Rosati, Tetrahedron Lett. 39, 8159 (1998)

    Article  CAS  Google Scholar 

  19. Y.J. Kim, R.S. Varma, Tetrahedron Lett. 46, 1467 (2005)

    Article  CAS  Google Scholar 

  20. A.T. Khan, E. Mondal, B.M. Borah, S. Ghosh, Eur. J. Org. Chem. 21, 4113 (2003)

    Article  CAS  Google Scholar 

  21. A.A. Manesh, A. Khazaei, M. Gohari, M. Chegeni, S. Saednia, Iran. Chem. Commun. 5, 308 (2017)

    Google Scholar 

  22. I. Mohammadpoor-Baltork, M. Moghadam, S. Tangestaninejad, V. Mirkhani, A.R. Khosropour, A. Mirjafari, J. Iran. Chem. Soc. 8, 513 (2011)

    Article  CAS  Google Scholar 

  23. I. Mohammadpoor-Baltork, M. Moghadam, S. Tangestaninejad, V. Mirkhani, A.R. Khosropour, A.R. Mirjafari, C. R. Chimie. 14, 568 (2011)

    Article  CAS  Google Scholar 

  24. A.K. Kabra, M. Huuhtanen, R.L. Keiski, G.D. Yadav, React. Chem. Eng. 1, 330 (2016)

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  26. G. Zhu, X. Qiu, Y. Zhao, Y. Qian, Y. Pang, X. Ouyang, Bioresour. Technol. 218, 718 (2016)

    Article  CAS  PubMed  Google Scholar 

  27. T. Jiang, B.X. Han, Angew. Chem. Int. Ed. 47, 1127 (2008)

    Article  CAS  Google Scholar 

  28. J.J. Peng, Y.Q. Deng, New J. Chem. 25, 639 (2001)

    Article  CAS  Google Scholar 

  29. M.A. Zolfigol, A. Khazaei, A.R. Moosavi-Zare, A. Zare, J. Iran. Chem. Soc. 7, 646 (2010)

    Article  CAS  Google Scholar 

  30. M.M. Heravi, H.A. Oskooie, Z. Latifi, H. Hamidi, Adv. J. Chem. A 1, 7 (2018)

    Google Scholar 

  31. A. Sarkar, S.R. Roy, N. Parikh, A.K. Chakrabarti, J. Org. Chem. 75, 7132 (2011)

    Article  CAS  Google Scholar 

  32. Y. wei, C. Keke, Z. Xiaofang, K. Yingying, T. Xiujuan, H. Xiaoxinang, J. Int. Eng. Chem. 20, 185 (2015)

  33. Y. Cao, H. Zhou, J. Li, Renew. Sust. Energ. Rev. 58, 871 (2016)

    Article  CAS  Google Scholar 

  34. Z. Duan, Y. Gu, Y. Deng, Synth. Commun. 35, 1939 (2005)

    Article  CAS  Google Scholar 

  35. A.R. Hajipour, Z. Nasresfahani, Synth. Commun. 42, 1995 (2012)

    Article  CAS  Google Scholar 

  36. N. Azizi, M. Abdoli-Senejani, F. Abbasi, Tetrahedron Lett. 57, 5009 (2016)

    Article  CAS  Google Scholar 

  37. A.R. Hajipoura, Gh. Azizib, Iran. J. Catal. 4, 213 (2014)

    Google Scholar 

  38. F. Shirini, S.V. Atghia, M.G. Jirdehi, Catal. Commun. 18, 5 (2012)

    Article  CAS  Google Scholar 

  39. J.S. Yadav, B.V.S. Reddy, D. Gnaneshwar, New J. Chem. 27, 202 (2003)

    Article  CAS  Google Scholar 

  40. J. Ashtarian, R. Heydari, M.-T. Maghsoodlou, A. Yazdani-Elah-Abadi, Iran. J. Sci. Technol. A. 44, 51 (2020)

    Article  Google Scholar 

  41. Z. Sharifi, N. Daneshvar, M.S.N. Langarudi, F. Shirini, Res. Chem. Intermed. 45, 4941 (2019)

    Article  CAS  Google Scholar 

  42. R. Karimi Chayjani, N. Daneshvar, F. Shirini, H. Tajik, Res. Chem. Intermed. 45, 2471 (2019)

    Article  CAS  Google Scholar 

  43. N. Daneshvar, M. Nasiri, M. Shirzad, M.S.N. Langarudi, F. Shirini, H. Tajik, New J. Chem. 42, 9744 (2018)

    Article  CAS  Google Scholar 

  44. F. Shirini, M.S.N. Langarudi, N. Daneshvar, N. Jamasbi, M. Irankhah-Khanghah, J. Mol. Struct. 1161, 366 (2018)

    Article  CAS  Google Scholar 

  45. M. Zabihzadeh, A. Omidi, F. Shirini, H. Tajik, M.S.N. Langarudi, J. Mol. Struct. 1206, 127730 (2020)

    Article  CAS  Google Scholar 

  46. C.H. Lin, M.Y. Wan, Y.M. Huang, Catal. Lett. 87, 253 (2003)

    Article  CAS  Google Scholar 

  47. M. Moghadam, Sh. Tangestaninejad, V. Mirkhani, I. Mohammadpoor-Baltork, Sh. Chahardahcheric, Z. Tavakoli, J. Organomet. Chem. 693, 2041 (2008)

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  49. F. Shirini, E. Mollarazi, Catal. Commun. 8, 1393 (2007)

    Article  CAS  Google Scholar 

  50. H. Tajik, K. Niknam, S. Karimian, Iran. J. Catal. 3, 107 (2013)

    Google Scholar 

  51. F. Shirini, M. Abedini, J. Iran. Chem. Soc. 5, 87 (2008)

    Article  Google Scholar 

  52. F. Shirini, M. Abedini, M. Shamsi-Sani, M. Seddighi, Iran. J. Catal. 5, 373 (2015)

    CAS  Google Scholar 

  53. M.M. Heravi, M. Haghighi, F. Derikvand, F.F. Bamoharram, Synth. Commun. 36, 3103 (2006)

    Article  CAS  Google Scholar 

  54. I. Mohammadpoor-Baltork, M. Moghadam, S. Tangestaninejad, V. Mirkhani, A. Mirjafari, Can. J. Chem. 86, 831 (2008)

    Article  CAS  Google Scholar 

Download references

Acknowledgements

We are thankful to the Research Council of the University of Guilan for the partial support of this research.

Author information

Authors and Affiliations

  1. Department of Chemistry, College of Science, University of Guilan, University, Campus 2, 41335-1914, Rasht, Iran

    Akram Rahmanzadeh, Nader Daneshvar, Farhad Shirini & Hassan Tajik

Authors
  1. Akram Rahmanzadeh
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Nader Daneshvar
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Farhad Shirini
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Hassan Tajik
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Farhad Shirini.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Rahmanzadeh, A., Daneshvar, N., Shirini, F. et al. Comparison of the efficiency of two dicationic ionic liquids catalysts based on perchloric acid for the protection of alcohols. J IRAN CHEM SOC 18, 3295–3302 (2021). https://doi.org/10.1007/s13738-021-02267-z

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s13738-021-02267-z

Keywords

Search

Navigation