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An acyl azide is a type of chemical compound that contains three nitrogen atoms in a group represented as (-N₃). These compounds are derived from hydrazoic acid, where a hydrocarbon group or an acyl group replaces the hydrogen atom. Acyl azides are generally more stable than inorganic and alkyl azides.1

When heated, acyl azides undergo a molecular rearrangement known as the Curtius rearrangement, forming isocyanates. If water is present, the isocyanate is then converted into an amine that has one fewer carbon atom than the original acyl azide. Acyl azides can be synthesized by reacting nitrous acid with acid hydrazides or by reacting an acyl chloride with sodium azide.1

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