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Unexpected conversion of alkyl azides to alkyl iodides and of aryl azides to N-tert-butyl anilines
Authors:Julien Maury  Laurence Feray  Michèle P Bertrand  Ajoy Kapat  Philippe Renaud
Institution:a Aix-Marseille Université, CNRS, Institut de Chimie Radicalaire, UMR 7273, Equipe Chimie Moléculaire Organique, boite 562, Faculté des Sciences et Techniques de Saint Jérôme, Av. Escadrille Normandie Niemen, 13397 Marseille Cedex 20, France
b University of Bern, Department of Chemistry and Biochemistry, Freiestrasse 3, CH-3012 Bern, Switzerland
Abstract:In the presence of tert-butyl iodide, alkyl azides are converted into the corresponding iodides at room temperature, whereas, N-t-Bu anilines are obtained from aryl azides under the same experimental conditions. A mechanism is proposed to explain this unusual reactivity.
Keywords:Alkyl and aryl azides  tert-Butyl iodide  Alkyl iodides  N-t-Bu anilines
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