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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:

L. Marinescu, J. Thinggaard, I. B. Thomsen, M. Bols, J. Org. Chem., 2003, 68, 9453-9455.

DOI: 10.1021/jo035163v

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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.

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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