Octet / Reactions
Curtius Rearrangement
Curtius Rearrangement (Rearrangement.) Converts CC(=O)N=[N+]=[N-] to CN=C=O using Heat or photolysis. Conditions: Heat or UV light.
Rearrangement
Reaction details
Name
Curtius Rearrangement
Type
Rearrangement
Starting Material
CC(=O)N=[N+]=[N-]
Product
CN=C=O
Reagents
Heat or photolysis
Conditions
Heat or UV light
Mechanism
- Smiles
CC(=O)N=[N+]=[N-]
- Description
Acyl azide (from acid chloride + NaN₃)
- Smiles
CN=C=O
- Description
Loss of N₂, migration gives isocyanate
Tips
Acyl azide → Isocyanate (+ N₂)
Isocyanate + H₂O → Amine (with CO₂ loss)
Isocyanate + ROH → Carbamate
Net: RCOOH → RNH₂ (one carbon shorter)
Related Reactions
hofmann-rearrangement
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