Synthesis 2004(18): 2959-2961  
DOI: 10.1055/s-2004-834919
SHORTPAPER
© Georg Thieme Verlag Stuttgart · New York

1,3-Dibromo-5,5-Dimethylhydantoin [DBDMH] as an Efficient and Selective Agent for the Oxidation of Thiols to Disulfides in Solution or under Solvent-Free Conditions

Ardeshir Khazaei*, Mohammad Ali Zolfigol, Amin Rostami
Department of Chemistry, Faculty of Science, Bu-Ali Sina University, P.O. Box 65174-4119, Hamedan, Iran
e-Mail: a_khazaei@basu.ac.ir;
Further Information

Publication History

Received 11 June 2004
Publication Date:
17 November 2004 (online)

Abstract

A useful method for oxidation of various thiols to their corresponding disulfides with 1,3-dibromo-5,5-dimethylhydantoin (DBDMH) in very short reaction times and mild conditions under both solution and solvent-free conditions is described.

    References

  • 1 Capozzi G. Modena G. Patai S. The Chemistry of the Thiol Group   Part 2:  Patai S. Wiley; New York: 1974.  p.785 
  • 2 Jocelyn DC. Biochemistry of the Thiol Group   Academic Press; New York: 1992.  p.1 
  • 3 Ramadas K. Srinivasan N. Synth. Commun.  1995,  25:  227 
  • 4a Lam J. Bilddose H. Christensen LP. Thomsen T. Acta. Chem. Scand. Ser. B  1989,  43:  799 
  • 4b Srivastav V. Gupta R. Guptam RR. Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem.  2000,  39:  223 
  • 4c Metzner P. Synthesis  1992,  1185 
  • 5a Firouzabadi H. Mohammadpoor-Baltork I. Bull. Chem. Soc. Jpn.  1992,  65:  1485 
  • 5b Iranpoor N. Firouzabadi H. Zolfigol MA. Synth. Commun.  1998,  28:  367 
  • 5c Iranpoor N. Zeynizadeh B. Synthesis  1999,  49 
  • 5d Sun Y.-H. Ko K.-Y. Bull. Korean Chem. Soc.  2000,  21:  669 
  • 5e Raghavan S. Rajender A. Joseph SC. Rasheed MA. Synth. Commun.  2001,  31:  1477 
  • 5f Salehi P. Farrokhi A. Gholizadeh M. Synth. Commun.  2001,  31:  2777 
  • 5g Arnaiz FJ. Aguado R. Pedrosa MR. Synthesis  2002,  856 
  • 5h Khodaei MM. Mohammadpoor-Baltork I. Nikoofar K. Bull. Korean Chem. Soc.  2003,  24:  885 
  • 5i Zeynizadeh B. Iranpoor N. J. Chin. Chem. Soc. (Taipei)  2003,  50:  849 
  • 5j Lezina OM. Rubtsova SA. Kuchin AV. Russ. Chem. Bull.  2003,  52:  1878 
  • 5k Chauhan SMS. Kumar A. Srinivas KA. Chem. Commun.  2003,  21:  2348 
  • 5l Tajbakhsh M. Hosseinzadeh R. Shakoori A. Tetrahedron Lett.  2004,  45:  1889 
  • 5m Hashemi MM. Karimi-Jaberi Z. Monatsh. Chem.  2004,  135:  416 
  • 6a Drabowicz J. Mikolajczyk M. Synthesis  1980,  32 
  • 6b Movassagh B. Lakouraj MM. Ghodrati K. Synth. Commun.  1999,  29:  3597 
  • 6c Kesavan V. Bonnet-Delpon D. Begue J.-P. Synthesis  2000,  223 
  • 6d Zolfigol MA. Synth. Commun.  2000,  30:  1593 
  • 6e Varma RS. Meshram HM. Dahiya R. Synth. Commun.  2000,  30:  1249 
  • 6f Zolfigol MA. Tetrahedron  2001,  57:  9509 
  • 6g Ali MH. McDermott M. Tetrahedron Lett.  2002,  43:  6271 
  • 6h Chen F.-E. Lu Y.-W. He Y.-P. Luo Y.-F. Yan M.-G. Synth. Commun.  2002,  32:  3487 
  • 6i Zolfigol MA. Shirini F. Ghorbani-Choghamarani A. Ghofrani E. Phosphorus, Sulfur Silicon Relat. Elem.  2003,  178:  1477 
  • 7a Khazaei A. Vaghei RG. Tetrahedron Lett.  2002,  43:  30733 
  • 7b Khazaei A. Vaghei RG. Tajbakhsh M. Tetrahedron Lett.  2001,  42:  59 
  • 7c Khazaei A. Shirdarreh A. Synth. Commun.  1999,  29:  4079 
  • 7d Khazaei A. Bridson K. Pitchard RG. Cryst. Struct. Commun. C5.  2001,  970 
  • 7e Khazaei A. Mehdipour E. Roodpeyma B. Iran. J. Chem. & Chem. Eng.  1995,  14:  77 
  • 7f Azarifar D. Zolfigol MA. Maleki B. Bull. Korean Chem. Soc.  2004,  25:  23 
  • 8 Corey EJ. Kim CU. J. Am. Chem. Soc.  1972,  94:  7586 
  • 9 FrØyen P. Synth. Commun.  1995,  25:  959 
  • 10 Poucher CJ. The Aldrich Library of NMR Spectra   Vol. 1:  Aldrich Chemical Company; Milwaukee USA: 1983.  p.465B