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The Nitrosation of Aliphatic Carbon Atoms

  1. Oscar Touster

Published Online: 15 MAR 2011

DOI: 10.1002/0471264180.or007.06

Organic Reactions

Organic Reactions

How to Cite

Touster, O. 2011. The Nitrosation of Aliphatic Carbon Atoms. Organic Reactions. 7:6:327–377.

Author Information

  1. Vanderbilt University School of Medicine

Publication History

  1. Published Online: 15 MAR 2011

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Abstract

The nitrosation reaction consists in the replacement of a hydrogen atom by the nitroso group with the formation of a nitroso or oximo derivative. With a few exceptions, the replacement of hydrogen on an aliphatic carbon atom requires the presence of an electron-attracting groups adjacent to the carbon to be nitrosated. Acyl, aroyl, carbonyl, carboxy, carbalkoxyl, nitrogen, cyano, imino, and aryl groups may serve as activators. Monoketones are readily converted into alpha-oximino ketones, whereas monoesters containing no other activating groups do not undergo the reaction. Victor Meyer discovered the reaction in 1873–1874.

Keywords:

  • nitrosation;
  • aliphatic carbon atoms;
  • ketones;
  • keto acids;
  • malonic acid;
  • nitriles;
  • arylacetic acid;
  • esters;
  • hydrocarbons;
  • nitro compounds;
  • synthetic applications;
  • experimental conditions