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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 least stable alkene (the one with the fewest substituents on the carbons of the double bond), called the Hofmann product, is formed. This tendency, known as the Hofmann alkene synthesis rule , is in contrast to usual elimination reactions, where Zaitsev's rule predicts the formation of the most stable alkene.
It is accompanied by carbocationic rearrangement reactions; Scheme 2. E1 reaction mechanism. An example in scheme 2 is the reaction of tert-butylbromide with potassium ethoxide in ethanol. E1 eliminations happen with highly substituted alkyl halides for two main reasons.
An example of the E1cB reaction mechanism in the degradation of a hemiketal under basic conditions. The E1cB elimination reaction is a type of elimination reaction which occurs under basic conditions, where the hydrogen to be removed is relatively acidic, while the leaving group (such as -OH or -OR) is a relatively poor one.
The resulting sodium salt of phthalamic acid is decarbonylated via a Hofmann rearrangement of the amide group, induced by hypochlorite: [15] C 6 H 4 (C(O)NH 2)CO 2 Na + HOCl → C 6 H 4 NH 2 CO 2 H + NaCl + CO 2. A related method involves treating phthalimide with sodium hypobromite in aqueous sodium hydroxide, followed by neutralization. [16]
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 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 ...