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Synthesis 2011(10): 1515-1525
DOI: 10.1055/s-0030-1260006
DOI: 10.1055/s-0030-1260006
FEATUREARTICLE
© Georg Thieme Verlag
Stuttgart ˙ New York
Hydrogen Peroxide and Arenediazonium Salts as Reagents for a Radical Beckmann-Type Rearrangement
Further Information
Publication History
Received
20 December 2010
Publication Date:
15 April 2011 (online)


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
- Supporting Information for this article is available online:
- Supporting Information