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Russian Chemical Bulletin

, Volume 53, Issue 9, pp 1846–1858 | Cite as

New reactions of γ-halocarbanions: underestimated reactive intermediates in organic synthesis

  • M. Barbasiewicz
  • M. Judka
  • M. Makosza
Article

Abstract

Short-lived γ-halocarbanions can be trapped by active electrophiles such as aldehydes, imines, and Michael acceptors to give anionic adducts, which undergo intramolecular substitution to give substituted tetrahydrofurans, pyrrolidines, and cyclopentanes. This has underlain a new method for the synthesis of these valuable ring systems. We have determined the acidity of the γ-halocarbanion precursors and have shown that the halogen atoms in the γ-position relative to the carbanion center exert a significant stabilizing effect on the carbanion.

Key words

carbanions tetrahydrofurans pyrrolidines cyclopentanes cyclizations pKa values of carbanion precursors 

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Copyright information

© Springer Science+Business Media, Inc. 2004

Authors and Affiliations

  • M. Barbasiewicz
    • 1
  • M. Judka
    • 1
  • M. Makosza
    • 1
  1. 1.Institute of Organic ChemistryPolish Academy of SciencesWarsaw 42Poland

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