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Published TCIMAIL newest issue No.197
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Hofmann Rearrangement Reaction
The Hofmann rearrangement is well known reaction used to synthesize primary amines from amides via a one carbon degradation. In this reaction, amides react with bromine and strong base which subsequently rearranges to give an isocyanate. Hydrolysis of the isocyanate affords an amine, whereas carbamate is provided by treatment with an alcohol. These mechanistic steps lend well to utilizing the Hoffman rearrangement as a method for amine protection. The Curtius rearrangement is a similar well known reaction.
- Reagents:
- Bromine, Sodium hydroxide, Alcohols
- Reactants:
- Primary amides
- Products:
- Primary amines, Carbamates
- Scheme:
-
- Original literature:
-
- Ueber die Einwirkung des Broms in alkalischer Lösung auf Amide
- Review literature:
-
- Perspectives on the synthesis of organic carbamates
