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Russian Chemical Bulletin

, Volume 43, Issue 12, pp 2065–2069 | Cite as

Reactions of alkylenebisbromomalonates with nucleophiles

  • R. G. Kostyanovsky
  • O. N. Krutius
  • Yu. I. El'natanov
Organic Chemistry
  • 50 Downloads

Abstract

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 of 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 acids 

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Copyright information

© Plenum Publishing Corporation 1995

Authors and Affiliations

  • R. G. Kostyanovsky
    • 1
  • O. N. Krutius
    • 1
  • Yu. I. El'natanov
    • 1
  1. 1.N. N. Semenov Institute of Chemical PhysicsRussian Academy of SciencesMoscowRussian Federation

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