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Aza-Claisen Rearrangement

Published Online: 15 SEP 2010

DOI: 10.1002/9780470638859.conrr029

Comprehensive Organic Name Reactions and Reagents

Comprehensive Organic Name Reactions and Reagents

How to Cite

2010. Aza-Claisen Rearrangement. Comprehensive Organic Name Reactions and Reagents. 29:123–127.

Publication History

  1. Published Online: 15 SEP 2010

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Abstract

In the aza-Claisen rearrangement cleavage of one bond and the formation of a new bond take place. However, in this reaction, one allyl carbon atom is displaced by a nitrogen atom and the carbon-nitrogen bond is the bond to break. The nitrogen atom in aza-Claisen rearrangement has been reported either in a heterocycle or a quaternary amine (ammonium salt). The extension of heterocycle ring or cleavage of ammonium salt has been found to be the important factor which drive this reaction. The reaction between N-methylpyrrole and dimethyl acetylenedicarboxylate (DMAD) is one of the earliest reaction of of the aza-Claisen rearrangement. This reaction has wide application for the synthesis of variety types of nitrogen-containing compounds

Keywords:

  • N-methylpyrrole;
  • dimethyl acetylenedicarboxylate (DMAD);
  • nitrogen-containing heterocycle;
  • epimerization