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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. [ 1 ] [ 2 ] [ 3 ] The reaction involves oxidation of the nitrogen followed by rearrangement of the carbonyl and nitrogen to give an isocyanate intermediate.
The Hofmann rearrangement is a decarbonylation reaction whereby an amide is converted to an amine by way of an isocyanate intermediate. It is usually carried out under strongly basic conditions. It is usually carried out under strongly basic conditions.
The Cope elimination is very similar to the Hofmann elimination in principle, but occurs under milder conditions. It also favors the formation of the Hofmann product, and for the same reasons. [3] An example of a Hofmann elimination (not involving a contrast between a Zaitsev product and a Hofmann product) is the synthesis of trans-cyclooctene. [4]
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The reaction mechanism is that of the related Hofmann degradation. [2] Weermann degradation mechanism of Hydroxy-Carbonsäureamide. At first the carbonic acid amide (1) reacts with the sodium hypochlorite. After the separation of water and chloride an amine with a free bond is built 2. The intermediate (3) is generated by rearrangement. In the ...
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