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The Michael Reaction

  1. Ernst D. Bergmann1,
  2. David Ginsburg2,
  3. Raphael Pappo3

Published Online: 15 MAR 2011

DOI: 10.1002/0471264180.or010.03

Organic Reactions

Organic Reactions

How to Cite

Bergmann, E. D., Ginsburg, D. and Pappo, R. 2011. The Michael Reaction . Organic Reactions. 10:3:179–556.

Author Information

  1. 1

    Ministry of Defence, Scientific Department, Tel-Aviv

  2. 2

    Israel Institute of Technology, Chemistry Department, Haifa

  3. 3

    Hebrew University, Department of Organic Chemistry, Jerusalem

Publication History

  1. Published Online: 15 MAR 2011

Abstract

The Michael condensation in its original scope is the addition of an addend or donor containing an alpha-hydrogen atom in the system O[DOUBLE BOND]C[BOND]CH to a carbon-carbon double bond that forms part of a conjugated system of the general formula C[DOUBLE BOND]C[BOND]C[DOUBLE BOND]O in an acceptor. The condensation takes place under the influence of alkaline reagents, typically alkali metal alkoxides. The range of addends is very broad. Typical acceptors are alpha, beta-unsaturated aldehydes, keotnes, and acid derivatives. As an extension of the original scope, the Michael condensation has come to be understood to include addends and acceptors activated by groups other than carbonyl and carboxalkoxy. The wider scope is encompassed in this survey.

Keywords:

  • Michael reaction;
  • side reaction;
  • adduct;
  • bridged intermediates;
  • cyclopropane derivatives;
  • Michael condensation;
  • ketones;
  • esters;
  • cycloalkanones;
  • cycloalkenes;
  • Robinson's modification;
  • aromatic rings systems;
  • rings;
  • pyrroles;
  • piperidines;
  • pyrrolizidines;
  • amino salts;
  • experimental conditions