Radical Azidonation of Aldehydes
Lavinia Marinescu, Jacob Thinggaard, Ib B. Thomsen and Mikael Bols*
*Department of Chemistry, Aarhus University, Langelandsgade 140, DK-8000
Aarhus, Denmark, Email: bols
kemi.ku.dk
L. Marinescu, J. Thinggaard, I. B. Thomsen, M. Bols, J. Org. Chem., 2003, 68, 9453-9455.
DOI: 10.1021/jo035163v (free Supporting Information)
see article for more examples
Abstract
Aliphatic and aromatic aldehydes can be converted to acyl azides by treatment with iodine azide. If the reaction is performed at reflux, Curtius rearrangement occurs and carbamoyl azides are obtained directly from the aldehyde in good yield.
see article for more examples
proposed mechanism
Safe radical azidonation using polystyrene supported diazidoiodate(I)
L. G. Marinescu, C. M. Pedersen, M. Bols, Tetrahedron, 2005, 61, 123-127.
Key Words
acyl azides, carbamoyl azides, urea derivatives, Curtius Rearrangement
ID: J42-Y2003-960
