Synthesis 2004(2): 227-232  
DOI: 10.1055/s-2004-44387
PAPER
© Georg Thieme Verlag Stuttgart · New York

A Selective, Convenient, and Efficient Conversion of Sulfides to Sulfoxides

Wei Liang Xu*, Yun Zheng Li, Qing Shan Zhang, He Sun Zhu
School of Chemical Engineering and Environment, Beijing Institute of Technology, Beijing 100081, P. R. China
Fax: +86(10)68913293; e-Mail: [email protected];
Weitere Informationen

Publikationsverlauf

Received 16 October 2003
Publikationsdatum:
18. Dezember 2003 (online)

Abstract

A novel, convenient and chemoselective procedure for oxidizing sulfides to sulfoxides with 30% aqueous H2O2 in phenol at room temperature is described. The procedure is very simple and no strict conditions were required for the selective conversion without affecting the functional groups even including the highly reactive aldehyde group. The reactions proceeded very quickly in excellent yields. Some experimental evidences are presented describing the role of the solvent.

    References

  • 1a Fuhrhop J. Penzlin G. Organic Synthesis. Concepts, Methods, Starting Material   2nd ed.:  VCH; Weinheim: 1994. 
  • 1b Block E. Reactions of Organosulfur Compounds   Academic Press; New York: 1978. 
  • 2 Ravikumar KS. Barbier F. Bégué J.-P. Bonnet-Delpon D. J. Fluorine Chem.  1999,  95:  123 
  • 3a Martin SE. Rossi LI. Tetrahedron Lett.  2001,  42:  7174 
  • 3b Ali MH. Stevens WC. Synthesis  1997,  764 
  • 3c Batigalhia F. Zaldini-Hernandes M. Ferreira AG. Malvestiti I. Cass QB. Tetrahedron  2001,  57:  9669 
  • 3d Lindén AA. Krüger L. Bäckvall J.-E. J. Org. Chem.  2003,  68:  5890 
  • 3e Iranpoor N. Firouzabadi H. Pourali A.-R. Tetrahedron  2002,  58:  5179 
  • 3f Khurana JM. Panda AK. Ray A. Gogia A. Org. Prep. Proced. Int.  1996,  28:  234 
  • 3g Varma RS. Saini RK. Meshram HM. Tetrahedron Lett.  1997,  38:  6525 
  • 3h Breton GW. Fields JD. Kropp PJ. Tetrahedron Lett.  1995,  36:  3825 
  • 3i Mckillop A. Tarbin JA. Tetrahedron Lett.  1983,  24:  1505 
  • 3j Leonard NJ. Johnson CR. J. Org. Chem.  1962,  27:  282 
  • 3k Goheen DW. Bennett CF. J. Org. Chem.  1961,  26:  1331 
  • 3l Kaldor SW. Hammond M. Tetrahedron Lett.  1991,  32:  5043 
  • 3m Mckillop A. Tarbin JA. Tetrahedron Lett.  1983,  24:  1505 
  • 3n Trost BM. Curran DP. Tetrahedron Lett.  1981,  22:  1287 
  • 3o Kennedy RJ. Stock AM. J. Org. Chem.  1960,  25:  1901 
  • 3p Djerassi C. Engle RR. J. Am. Chem. Soc.  1953,  75:  3838 
  • 3q Fringuelli F. Pellegrino R. Piermatti O. Pizzo F. Synth. Commun.  1994,  24:  2665 
  • 4 Schultz HS. Freyermuth HB. Buc SR. J. Chem. Soc.  1963,  1140 
  • 5 Collins FM. Lucy AR. Sharp C. J. Mol. Catal., A: Chem.  1997,  117:  397 
  • 6 Ravikumar KS. Bégué J.-P. Bonnet-Delpon D. Tetrahedron Lett.  1998,  39:  3141 
  • 7 Drabowicz J. Mikojajczyk M. Synth. Commun.  1981,  11:  1025 
  • 8 Parker AJ. J. Chem. Soc.  1961,  1328 
  • 9 Streitwieser A. Chem. Rev.  1956,  56: 571 
  • 10a Kosower EM. J. Am. Chem. Soc.  1958,  80:  3253 
  • 10b Kosower EM. J. Am. Chem. Soc.  1958,  80:  3267 
  • 11 Watanabe M. Fuoss RM. J. Am. Chem. Soc.  1956,  78:  527