Synlett 2008(11): 1742-1743  
DOI: 10.1055/s-2008-1067023
SPOTLIGHT
© Georg Thieme Verlag Stuttgart · New York

N-Chlorosaccharin (NCSac): A Useful and Alternative Reagent in Organic Synthesis

Paola Ervatti Gama*
Centro de Tecnologia, Bloco A, Instituto de Química, Universidade Federal do Rio de Janeiro, 21941-590 Rio de Janeiro, Brazil
e-Mail: paolagama@hotmail.com;
Further Information

Publication History

Publication Date:
11 June 2008 (online)

Introduction

N-Chlorosaccharin (NCSac) belongs to the class of N-haloimides and is of great importance in synthetic organic chemistry since its chloro substituent is more electrophilic than the chlorine in the structurally analogous N-chlorosuccinimide. [1] NCSac is stable, crystalline, soluble in most common organic solvents; it is a commercially available, relatively inexpensive reagent and commonly used in diverse organic transformations, such as halogenation, [2] [3] co-halogenation, [1] [2] [4] addition, [5] oxidation, [6a] [7] allylic and benzylic halogenation. [6a]

Preparation: NCSac can be easily prepared from sodium saccharinate in many different ways; [6] only the green methodology is presented here. [8] This route starts from sodium saccharinate and potassium chloride in the presence of oxone® and water as solvent, resulting in moderate yields. [8]

Scheme 1 Green route for NCSac synthesis

    References

  • 1 de Souza SPL. da Silva JFM. de Mattos MCS. Química Nova  2006,  29:  1061 
  • 2 de Souza SPL. da Silva JFM. de Mattos MCS. J. Braz. Chem. Soc.  2003,  14:  832 
  • 3 de Souza SPL. da Silva JFM. de Mattos MCS. Heterocycl. Commun.  2003,  9:  31 
  • 4 Dolenc D. Sket B. Synlett  1995,  327 
  • 5a Booker-Milburn I. Guly DJ. Cox B. Procopiou PA. Org. Lett.  2003,  5:  3313 
  • 5b Iranpoor NI. Firouzabadi H. Azadi R. Ebrahimzadeh F. Can. J. Chem.  2006,  69 
  • 6a Bachhawat JM. Koul AK. Prashad B. Ramegowda NS. Narang CK. Mathur NK. Indian J. Chem.  1973,  11:  609 
  • 6b Bachhawat JM. Mathur NK. Indian J. Chem.  1971,  9:  1335 
  • 6c Gakh AA. Romaniko SV. Ugrak BI. Fanzilberg AA. Tetrahedron  1991,  47:  7447 
  • 6d Ziegler K. Spath A. Schaaf E. Schumann W. Winkelmann E. Justus Liebigs Ann. Chem.  1942,  551, 80 
  • 7 Farook NAM. J. Solution Chem.  2007,  36:  345 
  • 8 de Souza SPL. da Silva JFM. de Mattos MCS. Synth. Commun.  2003,  33:  935