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Wibaut-Arens Alkylation

(Wibaut-Arens Reaction)

Published Online: 15 SEP 2010

DOI: 10.1002/9780470638859.conrr668

Comprehensive Organic Name Reactions and Reagents

Comprehensive Organic Name Reactions and Reagents

How to Cite

2010. Wibaut-Arens Alkylation. Comprehensive Organic Name Reactions and Reagents. 668:2998–3002.

Publication History

  1. Published Online: 15 SEP 2010

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Abstract

The preparation of 4-ethylpyridine by reductive alkylation of pyridine with acetic anhydride and zinc dust is known as the Wibaut–Arens alkylation or Wibau–Arens reaction. All the mechanistic features of this reaction have been discussed. It has been reported that intermediate decomposes to give equal amount of pyridine and 4-acetylpyridine, and the latter is then reduced to 4-ethylpyridine by zinc. Due to the steric hindrance for the potential dimerization of 2-position radical, 2-ethylpyridine has never been obtained from this reaction. This reaction has been modified by the treatment of pyridine with acid anhydride and iron instead of zinc. This reaction is useful in the preparation of pyridine derivatives, especially for the isonicotinic acid derivatives.

Keywords:

  • N,N′ -diacetyl-1,4,1′,4′-tetrahydro-4,4′-dipyridyl;
  • 4-ethylpyridine;
  • zinc;
  • iron