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.