Vicarious Nucleophilic Substitution of Hydrogen in Nitroarenes with in situ Generated Carbanions of 1-Methyl-3-chloro-1,3-dihydro-2,1-benzisothiazole 2,2-Dioxides

Abstract

Base-induced transformation of an equimolar mixture of 1-alkyl-1,3-dihydro-2,1-benzisothiazole 2,2-dioxides (benzosul­tams) and their 3,3-dichloro derivatives furnishes 1-alkyl-3-chloro-1,3-dihydro-2,1-benzisothiazole 2,2-dioxides which react with nitroarenes according to the vicarious nucleophilic substiution of hydrogen (VNS) mechanism giving 3-(nitroaryl)benzosultams.

Key words

benzosultams - halogenation - nitro compounds - carbanions - nucleophilic aromatic substitution

References

• 1 For a review on benzosultams, see: Wojciechowski K. Heterocycles  2002,  57:  1717 
• 2 For a review on aza-ortho-xylylenes, see: Wojciechowski K. Eur. J. Org. Chem.  2001,  3587 
• 3 Wojciechowski K. Synth. Commun.  1997,  26:  135 
• 4 Wojciechowski K. Pol. J. Chem.  1992,  66:  1121 
• For recent reviews on vicarious nucleophilic substitution of hydrogen, see:
• 5a Mąkosza M. Wojciechowski K. Liebigs Ann./Recueil  1997,  1805 
• 5b Mąkosza M. Kwast A. J. Phys. Org. Chem.  1998,  11:  341 
• 5c Mąkosza M. Wojciechowski K. Heterocycles  2001,  54:  445 
• 6a Kattenberg J. de Waard ER. Huisman HO. Tetrahedron  1973,  29:  4149 
• 6b For a review on chlorination of carbanions, see: Abele E. Lukevics E. Org. Prep. Proc. Int.  1999,  31:  359 
• 7 Wojciechowski K. Siedlecka U. Modrzejewska H. Kosiński S. Tetrahedron  2002,  58:  7583 
• 8 Mąkosza M. Goliński J. Synthesis  1983,  1023 
• 9 Mąkosza M. Goliński J. Baran J. J. Org. Chem.  1984,  49:  1488 
• 10 Bunnett JF. Kato T. Flynn RR. Skorcz JA. J. Org. Chem.  1963,  28:  1