Radical Azidonation of Aldehydes

Lavinia Marinescu, Jacob Thinggaard, Ib B. Thomsen, and Mikael Bols*
Department of Chemistry, Aarhus University, Langelandsgade 140, DK-8000 Aarhus C, Denmark
J. Org. Chem., 2003, 68 (24), pp 9453–9455
DOI: 10.1021/jo035163v
Publication Date (Web): November 7, 2003
Copyright © 2003 American Chemical Society
*

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

, mb@chem.au.dk

Abstract

Abstract Image

Aliphatic and aromatic aldehydes can be converted to acyl azides by treatment with iodine azide at 0−25 °C. If the reaction is performed at reflux Curtius rearrangement occurs and carbamoyl azides are obtained in 70−97% yield from the aldehyde. The reaction was shown to have a radical mechanism.

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History

  • Published In Issue November 28, 2003
  • Received August 7, 2003

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