Reactions of alkylenebisbromomalonates with nucleophiles

Article abstract of DOI:10.1007/BF00700171

Treatment of alkylenebisbromomalonates with nucleophiles (AcOK, AgOH, KHCO3, 1,8-diazabicyclo<5.4.0>undec-7-ene, or Ph3P) results mainly in their debromination to give cycloalkane-1,1,2,2-tetracarboxylates.When H2O and acids are present, the reaction gives products of the substitution pf one or two bromine atoms by hydrogen.Alkaline hydrolysis results in oxacycloalkane-α,α,α',α'-tetracarboxylic acids.The reaction mechanism is discussed. - Key words: alkylenebisbromomalonates; nucleophilic and homolytic substitution; cycloalkane-1,1,2,2-tetracarboxylates; oxacycloalkane-α,α,α',α'-tetracarboxylic acid.