Synlett 2008(11): 1742-1743  
DOI: 10.1055/s-2008-1067023
© 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
Further Information

Publication History

Publication Date:
11 June 2008 (online)


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


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