Reactions of alkylenebisbromomalonates with nucleophiles

Treatment of alkylenebisbromomalonates with nucleophiles (AcOK, AgOH, KHCO₃, 1,8-diazabicyclo5.4.0]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 of one or two bromine atoms by hydrogen. Alkaline hydrolysis results in oxacycloalkane-α,α,α′,α′-tetracarboxylic acids. The reaction mechanism is discussed.