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The Coupling of Diazonium Salts with Aliphatic Carbon Atoms

  1. Stanley M. Parmerter

Published Online: 15 MAR 2011

DOI: 10.1002/0471264180.or010.01

Organic Reactions

Organic Reactions

How to Cite

Parmerter, S. M. 2011. The Coupling of Diazonium Salts with Aliphatic Carbon Atoms. Organic Reactions. 10:1:1–142.

Author Information

  1. Wheaton College

Publication History

  1. Published Online: 15 MAR 2011

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Abstract

A diazonium salt will couple with an aliphatic compound containing an activated carbon-hydrogen bond. This discussion is limited to those reactions in which both the nitrogen atoms of the diazonium salts are retained in the resulting molecule. The discussion is further limited by the exclusion of coupling reactions, which occur with the elimination of a group from an activated methinyl compound, the Japp-Klingemann reaction. These reactions are discussed in Chapter 2. Much of the early work with coupling was prompted by the desire to determine whether the products were of the azo or hydrazonestructure. It is difficult to establish the structures in such cases where the tautomeric forms are possible. It is generally considered that the hydrazone is the stable form.

Keywords:

  • coupling;
  • diazonium salts;
  • aliphatic carbon atoms;
  • ketones;
  • esters;
  • amides;
  • malonic acids;
  • arylacetic acids;
  • nitriles;
  • sulfones;
  • nitro compounds;
  • hydrocarbons;
  • hydraoznes;
  • heterocyclic compounds