The Journal of Organic Chemistry · 2003 · 95 citations · 2 references
Natural SciencesChemistryOrganic ChemistryOrganic SynthesisOxidation ReactionsRadical ReactionsAldehydesAzide Radical ChemistryAzide ReactivityIodine Radical ChemistryRadical Mechanisms
Aliphatic and aromatic aldehydes can be converted to acyl azides by treatment with iodine azide at 0-25 degrees 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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Francesca Fontana, Francesco Minisci, Ming Yan Yong et al. · Tetrahedron Letters · 1993 · 82 citations