Hoffmann bromamide degradation involves treating an amide with bromine in an aqueous or ethanolic solution of sodium hydroxide. This reaction leads to the migration of an alkyl or aryl group from the carbonyl carbon of the amide to the nitrogen atom, resulting in the formation of a primary amine with one less carbon than the starting amide.
How does the Hoffmann bromamide degradation reaction facilitate the preparation of primary amines, and what is the key transformation involved?
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The Hoffmann bromamide degradation reaction facilitates the preparation of primary amines by converting an amide to an amine. In this process, an amide is treated with bromine and a base, leading to the formation of an isocyanate intermediate. This isocyanate undergoes intramolecular rearrangement, resulting in a carbamate, which subsequently undergoes hydrolysis to yield the primary amine. The key transformation involved is the rearrangement of the isocyanate intermediate, which plays a crucial role in converting the amide functional group into the desired primary amine. This method is particularly useful for synthesizing primary amines from amides in a straightforward manner.