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Synfacts 2009(5): 0544-0544  
DOI: 10.1055/s-0028-1088192
Metal-Mediated Synthesis
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of N-Alkoxyamines from Nitroxide Radicals and Aldehydes

Contributor(s): Paul Knochel, Tobias Thaler
K.-U. Schoening*, W. Fischer, S. Hauck, A. Dichtl, M. Kuepfert
Ciba Inc., Basel, Switzerland
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Publikationsdatum:
22. April 2009 (online)

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Significance

A novel expedient method for the synthesis of 2,2,6,6-tetramethylpiperidine-based N-alkoxyamines has been disclosed. In this reaction aldehydes act as a superb source for alkyl radical species, avoiding selectivity problems which may occur with ketones as radical sources. This method was found to tolerate a broad variety of functional groups which are usually subject to radical reactions, such as C=C bonds, nitro, ­cyano and alcohol functionalities.