Synthesis 2011(18): 2941-2944  
DOI: 10.1055/s-0030-1260142
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

An Efficient Synthesis of Vinyl Sulfones from Alkenes and Aryl Sulfinates [¹]

Biswanath Das*, Maram Lingaiah, Kongara Damodar, Nisith Bhunia
Organic Chemistry Division-1, Indian Institute of Chemical Technology, Hyderabad 500 007, India
Fax: +91(40)27193198; e-Mail: biswanathdas@yahoo.com;
Further Information

Publication History

Received 11 May 2011
Publication Date:
28 July 2011 (online)

Abstract

Vinyl sulfones have been efficiently synthesized by treatment of alkenes with sodium arene sulfinates using potassium iodide and sodium periodate in the presence of a catalytic amount of acetic acid at room temperature. The products are formed in high yields (87-95%) within 2.5-8 hours.

1

Part 229 in the series ‘Studies on Novel Synthetic Methodologies’.

    References

  • 2a Fuchs PL. Braish TF. Chem. Rev.  1986,  86:  903 
  • 2b De Lucci O. Pasquato L. Tetrahedron  1988,  44:  6755 
  • 3a Bremner J. Julia M. Launay M. Stacino J.-P. Tetrahedron Lett.  1982,  23:  3265 
  • 3b Cuvigny T. Hevre Du Penhoat C. Julia M. Tetrahedron  1987,  43:  859 
  • 4a Toth JE. Hamann PR. Fuchs PL. J. Org. Chem.  1988,  53:  4694 
  • 4b Burkholder TP. Fuchs PL. J. Am. Chem. Soc.  1993,  112:  9601 
  • 4c Wardrop DJ. Fritz J. Org. Lett.  2006,  8:  3659 
  • 5 Meadows DC. Gervay-Hague J. Med. Res. Rev.  2006,  26:  793 
  • 6a Simpkins NS. Tetrahedron  1990,  46:  6951 
  • 6b Nair V. Augustine A. George TG. Nair LG. Tetrahedron Lett.  2001,  42:  6763 
  • 6c Katrun P. Chiampanichayakul S. Korworapan K. Pohmakotr M. Peutrakul V. Jaipetch T. Kuhakarn C. Eur. J. Org. Chem.  2010,  5633 
  • 6d Huang X. Duan D. Zheng W. J. Org. Chem.  2003,  68:  1958 
  • 6e Cacchi S. Fabrizi G. Gaggiamani A. Parisi LM. Bernini R. J. Org. Chem.  2004,  69:  5608 
  • 7a Das B. Damodar K. Bhunia N. J. Org. Chem.  2009,  74:  5607 
  • 7b Das B. Reddy ChR. Kumar DN. Krishnaiah M. Narender R. Synlett  2010,  391 
  • 7c Das B. Reddy GC. Balasubramanyam P. Salvanna N. Synthesis  2011,  816 
  • 8 Oriez R. Prunet J. Tetrahedron Lett.  2010,  51:  256 
  • 9 Emmanuvel L. Shukla RK. Sudalai A. Suryavanshi G. Shivaram S. Tetrahedron Lett.  2006,  47:  4793 
1

Part 229 in the series ‘Studies on Novel Synthetic Methodologies’.