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. {\textcopyright} 2012 Elsevier Ltd. All rights reserved.

Ajoy Kapat

Chemistry

(SoNS) School of Natural Sciences

Julien Maury

Laurence Feray

Mich{\`{e}}le Bertrand P.

Philippe Renaud

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Shiv Nadar University

Tetrahedron

Unexpected conversion of alkyl azides to alkyl iodides and of aryl azides to N-tert-butyl anilines