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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]
The Hofmann–Martius rearrangement in organic chemistry is a rearrangement reaction converting an N-alkylated aniline to the corresponding ortho and / or para aryl-alkylated aniline. The reaction requires heat, and the catalyst is an acid like hydrochloric acid .
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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 ...
The Hofmann–Löffler reaction (also referred to as Hofmann–Löffler–Freytag reaction, Löffler–Freytag reaction, Löffler–Hofmann reaction, as well as Löffler's method) is an organic reaction in which a cyclic amine 2 (pyrrolidine or, in some cases, piperidine) is generated by thermal or photochemical decomposition of N-halogenated amine 1 in the presence of a strong acid ...
Many of them include exceptions under Hofmann product (analogous to Zaytsev product). These include compounds having quaternary nitrogen and leaving groups like NR 3 +, SO 3 H, etc. In these eliminations the Hofmann product is preferred. In case the leaving group is halogens, except fluorine; others give the Zaytsev product. [clarification needed]