Synlett 2011(13): 1947-1948  
DOI: 10.1055/s-0030-1260969
SPOTLIGHT
© Georg Thieme Verlag Stuttgart ˙ New York

Sodium Dithionite

Xiao-Nan Zhang*
The College of Chemistry & Material Science, Hebei Normal University, Shijiazhuang 050016, P. R. of China
e-Mail: zhangxn0911@163.com;
Further Information

Publication History

Publication Date:
21 July 2011 (online)

Introduction

Sodium dithionite (also known as sodium hydrosulfite) is a versatile, inexpensive, safe and readily available reagent, which has been employed for more than 70 years. It has been used in biochemistry for the reduction of a variety of coenzymes and enzymes, and in organic synthesis to reduce several types of functional groups, such as aldehydes, ketones, imines, pyrazine, vinyl sulfones, nitro [¹] and azo groups, [²] oximes, [³] enones, [4] quinones, [5] and azides. [6] It was also found to be an efficient reagent for the reductive displacement of iodine [7] and reductive coupling of benzylic and allylic halides. [8] It has been also used as radical initiator to promote coupling of CF3CHClBr with 1,3,5-trimethoxybenzene, [9] the addition of 1-bromo-1-chloro-2,2,2-triuoroethane to the terminal double bond of allylbenzenes, [¹0] addition reaction of peruoroalkyl iodides with allenes, [¹¹] the reaction of polyfluoroalkyl iodides with alkenes, [¹²] addition of dialkyl phosphonodifluoromethyl radical onto unsaturated ketones, [¹³] fluoroalkylation of porphyrins [¹4] and vinyl ethers. [¹5] This reagent is found to be a useful reagent in the intramolecular Marschalk cyclization [¹6] and Claisen rearrangement. [¹7]

Sodium dithionite is now commercially available, but can also be prepared readily by the reaction of sodium bisulfite with zinc. [¹8] It is obtained as a white crystalline powder with a weak sulfurous odor. This compound is stable under most conditions, but it will decompose in hot water and in acid solutions.

Scheme 1

    References

  • 1a Pantos GD. Rodríguez-Morgade MS. Torres T. Lynch VM. Sessler JL. Chem. Commun.  2006,  2132 
  • 1b Al-Huniti MH. Zahra JA. El-Abadelah MM. Heterocycles  2007,  71:  411 
  • 1c Akiyama T. Uoyama H. Okujima T. Yamada H. Ono N. Uno H. Tetrahedron  2009,  65:  4345 
  • 2a Sydnes MO. Kuse M. Doi I. Isobe M. Tetrahedron  2009,  65:  3863 
  • 2b Sydnes LK. Elmi S. Heggen P. Holmelid B. Malthe-Sorensen D. Synlett  2007,  1695 
  • 3 Müller CE. Roegler C. Hockemeyer J. Heterocycles  2009,  79:  703 
  • 4 Li Z. Watkins EB. Liu H. Chittiboyina AG. Carvalho PB. Avery MA. J. Org. Chem.  2008,  73:  7764 
  • 5a Zhang YZ. Aouadi K. Chen G.-R. Praly J.-P. Synthesis  2007,  3473 
  • 5b Conchon E. Anizon F. Aboab B. Prudhomme M. Synthesis  2008,  2569 
  • 6 Mekheimer RA. Ibrahim YR. Ahmed EA. Frey W. Tetrahedron  2009,  65:  9843 
  • 7 Ponzinibbio A. Colinas PA. Lieberknecht A. Bravo RD. Lett. Org. Chem.  2006,  3:  459 
  • 8 Khurana JM. Bansal G. Sahoo PK. J. Chem. Res.  2004,  139 
  • 9 Dmowski W. Urbanczyk-Lipkowska Z. Wojcik D. J. Fluorine Chem.  2009,  130:  509 
  • 10 Ignatowska J. Dmowski W. J. Fluorine Chem.  2006,  127:  720 
  • 11 Ma ZC. Ma SM. Tetrahedron  2008,  64:  6500 
  • 12a Yang XY. Wang ZH. Fang X. Yang XJ. Wu FH. Shen YJ. Synthesis  2007,  1768 
  • 12b Ma ZC. Ma SM. Tetrahedron  2008,  64:  6500 
  • 13 Sene A. Diab S. Hienzsch A. Cahard D. Lequeux T. Synlett  2009,  981 
  • 14a Chen L. Jin LM. Guo CC. Chen QY. Synlett  2005,  963 
  • 14b Chen L. Jin LM. Xiao JC. Guo CC. Chen QY. Synlett  2007,  2096 
  • 15 Valdersnes S. Sydnes LK. Eur. J. Org. Chem.  2009,  5816 
  • 16 Suzuki F. Trenbeath S. Gleim RD. Sih CJ. J. Am. Chem. Soc.  1978,  100:  2272 
  • 17 Boddy IK. Boniface PJ. Cambie RC. Craw PA. Larsen DS. McDonald H. Rutledge PS. Woodgate PD. Tetrahedron Lett.  1982,  23:  4407 
  • 18 Pratt LA. Ind. Eng. Chem.  1924,  16:  676 
  • 19 Suzuki K. Hintermann L. Synthesis  2008,  2303 
  • 20 Yang DL. Fokas D. Li JZ. Yu LB. Baldino CM. Synthesis  2005,  47 
  • 21 Goswami S. Maity AC. Das NK. J. Sulfur Chem.  2007,  28:  233 
  • 22 Tang R.-Y. Zhong P. Lin Q.-L. Phosphorus Sulfur Silicon Relat. Elem.  2007,  182:  167 
  • 23 Dmowski W. Urbaczyk-Lipkowska Z. Wójcik D. J. Fluorine Chem.  2009,  130:  509 
  • 24 Mei Y.-Q. Liu J.-T. liu Z.-J. Synthesis  2007,  739 
  • 25 Li Y.-Q. Zhang L.-P. Monatsh. Chem.  2006,  137:  1315 
  • 26 Yang XL. Xu YL. Chen JX. Ding JC. Wu HY. Su WK. J. Chem. Res.  2009,  682