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The Hofmann rearrangement (Hofmann degradation) is the organic reaction of a primary amide to a primary amine with one less carbon atom. The reaction involves oxidation of the nitrogen followed by rearrangement of the carbonyl and nitrogen to give an isocyanate intermediate.
Hofmann rearrangement, also known as Hofmann degradation and not to be confused with Hofmann elimination, is the reaction of a primary amide with a halogen (chlorine or bromine) in strongly basic (sodium or potassium hydroxide) aqueous medium, which converts the amide to a primary amine. eg:
Hofmann rearrangement, also known as Hofmann degradation and not to be confused with Hofmann elimination, is the reaction of a primary amide with a halogen (chlorine or bromine) in strongly basic (sodium or potassium hydroxide) aqueous medium, which converts the amide to a primary amine.
The reaction is also called Hoffmann degradation of amide. The reaction of bromine with sodium hydroxide leads to the formation of sodium hypobromite (NaOBr) which in turn transforms the primary amide into an isocyanate intermediate.
Hofmann degradation of primary amides proceeds under very mild conditions in the presence of phenyl iodosyl bis(trifluoroacetate) (PIFA), and this rearrangement is particularly suitable for the formation of aminals derived from peptides and acylamino acids (Equation (44)) (< 84JOC4272, 85JMC769 > and references therein).
Hofmann rearrangement, also known as Hofmann degradation, is the reaction of a primary amide with a halogen (chlorine or bromine) in a strongly basic (sodium or potassium hydroxide) aqueous medium to convert the amide into a primary amine.
The Hofmann reaction: This is a rearrangement reaction that proceeds via an anionic active species. The reaction begins with the formation of N -halogenated amides, which are deprotonated by a base to form unstable alkali salts of N -halogenated amides with negative charges on the nitrogen atom.
