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Synthesis 1994; 1994(3): 242-244
DOI: 10.1055/s-1994-25447
short paper
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Synthesis of 2-(2,6-Dinitrophenyl)malonates, -acetates and acetonitrile by Copper-Mediated Vicarious Nucleophilic Substitution

Olof Haglund* , Martin Nilsson
  • *Department of Organic Chemistry, Chalmers University of Technology, S-412 96 Göteborg, Sweden
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Publikationsdatum:
27. September 2002 (online)

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A regioselective, vicarious nucleophilic substitution of 1,3-dinitrobenzene with α-bromo- and iodocarbanions proceeds in the presence of copper(I) tert-butoxide and pyridine giving 2,6-dinitrophenylmalonates, 2,6-dinitrophenylacetates or 2,6-dinitrophenylacetonitrile as the only isomers from bromomalonate esters, bromoacetate esters, iodoacetate esters or iodoacetonitrile, respectively. Without copper(I) tert-butoxide, the 4-substituted isomer is the only product. We believe that the reaction proceeds via a σ-adduct of 1,3-dinitrobenzene and halocarbanion from which hydrogen and halogen are eliminated. This elimination is dependent upon the concentration of copper(I) tert-butoxide.