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Carbon-Carbon Alkylations with Amines and Ammonium Salts

  1. James H. Brewster1,
  2. Ernest L. Eliel2

Published Online: 15 MAR 2011

DOI: 10.1002/0471264180.or007.03

Organic Reactions

Organic Reactions

How to Cite

Brewster, J. H. and Eliel, E. L. 2011. Carbon-Carbon Alkylations with Amines and Ammonium Salts. Organic Reactions. 7:3:99–197.

Author Information

  1. 1

    Purdue University

  2. 2

    University of Notre Dame

Publication History

  1. Published Online: 15 MAR 2011

Chemistry Terms

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This chapter is a review of those reactions of compounds containing labile amino groups in which a carbon-carbon bond is formed by amine replacement as, for example, in the alkylation of diethyl malonate by 1-dimethylamino-3-butanone. Attention has been given primarily to reactions of amines prepared by the Mannich reaction (Mannich bases), but for comparison, analogous reactions of simpler quaternary ammonium salts have been included.


  • carbon-carbon alkylations;
  • amines;
  • ammonium salts;
  • cyanide;
  • replacements;
  • active methyl groups;
  • active methylene groups;
  • indole;
  • quaternary salts;
  • organometallic compounds;
  • related reactions;
  • experimental conditions