Monatshefte für Chemie - Chemical Monthly

, Volume 145, Issue 7, pp 1151–1154 | Cite as

Simple and efficient oxidative transformation of thiols to disulfides using Cu(NO3)2·3H2O in H2O/AcOEt

  • Mohammad Soleiman-Beigi
  • Zahra Taherinia
Original Paper


A simple and efficient methodology is described for the preparation of symmetric disulfides from corresponding thiols in the presence of Cu(NO3)2 and in H2O/AcOEt (1:2). This process is environmentally friendly and economical because it does not use toxic or expensive reagents.

Graphical abstract


Disulfide Oxidative transformation Copper nitrate Aqueous media 



We gratefully acknowledge the financial support from the Ilam University Research Council.

Supplementary material

706_2014_1178_MOESM1_ESM.pdf (490 kb)
Supplementary material 1 (PDF 489 kb)


  1. 1.
    Metzner P, Thuillier A (1994) In: Katritzky AR, Meth-Cohn O, Rees CW (eds) Sulfur reagents in organic synthesis. Academic, San DiegoGoogle Scholar
  2. 2.
    Cremlyn RJ (1996) An introduction to organosulfur chemistry. Wiley, New YorkGoogle Scholar
  3. 3.
    Kondo T, Mitsudo T (2000) Chem Rev 100:3205CrossRefGoogle Scholar
  4. 4.
    Caldarelli SA, Hamel M, Duckert JF, Ouattara M, Calas M, Maynadier M, Wein S, Périgaud C, Pellet A, Vial HJ, Peyrottes S (2012) J Med Chem 55:4619CrossRefGoogle Scholar
  5. 5.
    Fisher HL (1950) Ind Eng Chem 42:1978CrossRefGoogle Scholar
  6. 6.
    Kishi Y, Nakatsuga S, Fukuyama T, Havel M (1973) J Am Chem Soc 95:6493CrossRefGoogle Scholar
  7. 7.
    Soleiman-Beigi M, Mohammadi F (2012) Tetrahedron Lett 53:4028CrossRefGoogle Scholar
  8. 8.
    Kabalka GW, Reddy MS, Yao M-L (2009) Tetrahedron Lett 50:7340CrossRefGoogle Scholar
  9. 9.
    Barba F, Ranz F, Batanero B (2009) Tetrahedron Lett 50:6798CrossRefGoogle Scholar
  10. 10.
    Bao M, Shimizu M (2003) Tetrahedron 59:9655CrossRefGoogle Scholar
  11. 11.
    Burlingame MA, Tom CTMB, Renslo AR (2011) ACS Comb Sci 13:205CrossRefGoogle Scholar
  12. 12.
    Stellenboom N, Hunter R, Caira MR (2010) Tetrahedron 66:3228CrossRefGoogle Scholar
  13. 13.
    Wang L, Li P, Zhou L (2002) Tetrahedron Lett 43:8141CrossRefGoogle Scholar
  14. 14.
    Szymelfejnik M, Demkowicz S, Rachon J, Witt D (2007) Synthesis 3528Google Scholar
  15. 15.
    Christoforou A, Nicolaou G, Elemes Y (2006) Tetrahedron Lett 47:9211CrossRefGoogle Scholar
  16. 16.
    Zolfigol MA (2001) Tetrahedron 57:9509CrossRefGoogle Scholar
  17. 17.
    Leino R, Lonnqvist J-E (2004) Tetrahedron Lett 45:8489CrossRefGoogle Scholar
  18. 18.
    Tanaka K, Ajiki K (2004) Tetrahedron Lett 45:25CrossRefGoogle Scholar
  19. 19.
    Hunter R, Caira M, Stellenboom N (2006) J Org Chem 71:8268CrossRefGoogle Scholar
  20. 20.
    Akdag A, Webb T, Worley SD (2006) Tetrahedron Lett 47:3509CrossRefGoogle Scholar
  21. 21.
    Vandavasi JK, Hu W-P, Chen C-Y, Wang J-J (2011) Tetrahedron 67:8895CrossRefGoogle Scholar
  22. 22.
    Ghorbani-Choghamarani A, Nikoorazm M, Godarziafshar H, Shokr A, Almasi H (2011) J Chem Sci 123:453CrossRefGoogle Scholar
  23. 23.
    Hosseinzadeh R, Tajbakhsh M, Khaledi H, Ghodrati K (2007) Monatsh Chem 138:871CrossRefGoogle Scholar
  24. 24.
    Silveira CC, Mendes SR (2007) Tetrahedron Lett 48:7469CrossRefGoogle Scholar
  25. 25.
    Shaabani A, Safari N, Shoghpour S, Rezayan AH (2008) Monatsh Chem 139:613CrossRefGoogle Scholar
  26. 26.
    Ozen R, Aydin F (2006) Monatsh Chem 137:307CrossRefGoogle Scholar
  27. 27.
    Ghorbani-Choghamarani A, Nikoorazm M, Godarziafshar H, Tahmasbi B (2009) Bull Korean Chem Soc 30:1388CrossRefGoogle Scholar
  28. 28.
    Tajbakhsh M, Hosseinzadeh R, Shakoori A (2004) Tetrahedron Lett 45:1889CrossRefGoogle Scholar
  29. 29.
    Ali MH, McDermoot M (2002) Tetrahedron Lett 43:6271CrossRefGoogle Scholar
  30. 30.
    Lenardo EJ, Lara RG, Silva MS, Jacob RG, Perin G (2007) Tetrahedron Lett 48:7668CrossRefGoogle Scholar
  31. 31.
    Eshghi E, Bakavoli M, Moradi H, Davoodnia A (2009) Phosphorus. Sulfur Silicon Relat Elem 184:3110CrossRefGoogle Scholar
  32. 32.
    Hashemi MM, Karimi-Jaberi Z (2004) Monatsh Chem 135:41CrossRefGoogle Scholar
  33. 33.
    Thurow S, Pereira VA, Martinez DM, Alves D, Perin G, Jacob RG, Lenardao EJ (2011) Tetrahedron Lett 52:640 (and references therein)CrossRefGoogle Scholar
  34. 34.
    Soleiman-Beigi M, Hemmati M (2013) Appl Organmet Chem 27:734CrossRefGoogle Scholar
  35. 35.
    Soleiman-Beigi M, Izadi A (2013) J Chem 725265Google Scholar
  36. 36.
    Shojaei AF, Alirezvani MA, Heravi M (2011) J Serb Chem Soc 76:955CrossRefGoogle Scholar
  37. 37.
    Montazerozohori M, Joohari S, Karami B, Haghighat N (2007) Molecules 12:694CrossRefGoogle Scholar

Copyright information

© Springer-Verlag Wien 2014

Authors and Affiliations

  1. 1.Department of ChemistryIlam UniversityIlamIran

Personalised recommendations