Synlett 2012(1): 157-158  
DOI: 10.1055/s-0031-1290104
SPOTLIGHT
© Georg Thieme Verlag Stuttgart ˙ New York

Rongalite

Jiu-Xi Chen*
College of Chemistry and Materials Engineering, Wenzhou University, Wenzhou 325035, P. R. of China
e-Mail: jiuxichen@wzu.edu.cn;
Further Information

Publication History

Publication Date:
13 December 2011 (online)

Introduction

Rongalite (also known as sodium formaldehyde sulfoxylate or sodium hydroxymethanesulfinate) is a versatile, inexpensive and readily available reagent, which has been employed twenty years ago. [¹] It is commonly used in the textile industry as a decolorizing agent. Several reports are available in the literature demonstrating its utility in organic synthesis. For example, rongalite is capable of producing the perfluoroalkyl free radicals via dehalogenation of alkyl halides, [²-4] such as direct perfluoroalkylation of pyridines, [5] coumarins [6] and 2-quinolones. [7] It has been also used for the cleavage of diaryl disuldes and diselenides generating the corresponding chalcogenolate species in situ that then undergo facile ring opening and acylation, affording β-hydroxy sulfides, [8] thioesters and selenoesters, [9] respectively. It was also found to be a sulf­oxylate dianion equivalent in the conversion of dihalides into sultine derivatives. [¹0-¹5]

Rongalite is commercially available, but it can also be readily prepared by reaction of formaldehyde with sodium sulfite. [¹6]

Scheme 1

    References

  • 1 Jarvis WF. Hoey MD. Finocchio AL. Dittmer DC. J. Org. Chem.  1988,  53:  5750 
  • 2 William RD. Maurice M. Samia AM. Tetrahedron Lett.  2001,  42:  4811 
  • 3 Wu FH. Huang BN. Lu L. Huang WY. J. Fluorine Chem.  1996,  80:  91 
  • 4 Anselmi E. Blazejewski JC. Tordeux M. Wakselman C. J. Fluorine Chem.  2000,  105:  41 
  • 5 Huang BN. Liu JT. Tetrahedron Lett.  1990,  31:  2711 
  • 6 Huang BN. Liu JT. Huang WY. J. Chem. Soc., Chem. Commun.  1990,  1781 
  • 7 Huang BN. Liu JT. Huang WY. J. Chem. Soc., Perkin Trans. 1  1994,  101 
  • 8 Lv GS. Li T. Hu RJ. Chen JX. Ding JC. Wu HY. J. Chem. Res.  2010,  549 
  • 9 Lin SM. Zhang JL. Chen JX. Gao WX. Ding JC. Su WK. Wu HY. J. Braz. Chem. Soc.  2010,  21:  1616 
  • 10 Dittmer DC. Hoey MD. The Chemistry of Sulphinic Acids Esters and Their Derivatives   Wiley; Chichester (UK): 1990.  p.239-273  
  • 11 Hoey MD. Dittmer DC. J. Org. Chem.  1991,  56:  1947 
  • 12 Liu WD. Chi CC. Pai IF. Wu AT. Chung WS.
    J. Org. Chem.  2002,  67:  9267 
  • 13 Kotha S. Khedkar P. J. Org. Chem.  2009,  74:  5667 
  • 14 Kotha S. Chavan AS. J. Org. Chem.  2010,  75:  4319 
  • 15 Kotha S. Meshram M. Heterocycles  2011,  82:  1663 
  • 16 Aleksandrova AN. Shibaeva IA. Budanov VV.
    Zh. Prikl. Khim. (St. Petersburg)  1989,  62:  2678 
  • 17 Dan WX. Deng HJ. Chen JX. Liu MC. Ding JC. Wu HY. Tetrahedron  2010,  66:  7384 
  • 18 Guo WX. Chen JX. Wu DZ. Ding JC. Chen F. Wu HY. Tetrahedron  2009,  65:  5240 
  • 19 Ganesh V. Chandrasekaran S. Synthesis  2009,  3267 
  • 20 Guo WX. Lv GS. Chen JX. Gao WX. Ding JC. Wu HY. Tetrahedron  2010,  66:  2297 
  • 21 Tang RY. Zhong P. Lin QL. Synthesis  2007,  85 
  • 22 Wang ZL. Tang RY. Luo PS. Deng CL. Zhong P. Li JH. Tetrahedron  2008,  64:  10670