Hydrogen Peroxide and
Arenediazonium Salts as Reagents for a Radical Beckmann-Type
Rearrangement

Agnes Prechter; Markus R. Heinrich

doi:10.1055/s-0030-1260006

FEATUREARTICLE

Hydrogen Peroxide and Arenediazonium Salts as Reagents for a Radical Beckmann-Type Rearrangement

Agnes Prechter, Markus R. Heinrich*
Department für Chemie und Pharmazie, Pharmazeutische Chemie, Friedrich-Alexander-Universität Erlangen-Nürnberg, Schuhstraße 19, 91052 Erlangen, Germany
Fax: +49(9131)8522585 ; e-Mail: Markus.Heinrich@medchem.uni-erlangen.de ;

Abstract

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Abstract

The reductive ring-opening of hydroperoxides derived from cyclic ketones leads to alkyl radicals which can effectively be trapped by arenediazonium salts. This synthetic transformation yielding azo carboxylic acids or lactams, after a reductive step, can be classified as a radical version of the well-known Beckmann rearrangement. In this article, we present results on the scope, the limitations and possible applications of this new reaction type.

Key words

radical reaction - rearrangement - ketones - carboxylic acids - azo compounds

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References

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