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The thermal decomposition of an acyl azide to an isocyanate and nitrogen gas is known as the Curtius rearrangement. The R group of the acyl azide migrates to its nearest nitrogen, releasing nitrogen gas to form the isocyanate product, which can further react with nucleophiles in solution, i.e. exposure to water produces a 1° amine.
- Reactant: Acyl Azide
- Product: Isocyanate
- Type of Reaction: Rearrangement
- Azide Monoliths as Convenient Flow Reactors for Efficient Curtius Rearrangement Reactions. Org. Biomol. Chem 2008, 6 (9), 1587–1593.
- Boc-Protected Amines via a Mild and Efficient One-Pot Curtius Rearrangement. Org. Lett 2005, 7 (19), 4107-4110.
- Acyl azide