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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.
In 2008 P.S. Baran et al. [48] reported a new method for the synthesis of 1,3-diols using a variant of the Hofmann–Löffler–Freytag reaction. In 2017, Nagib et al. [49] [50] reported a new method for the synthesis of 1,2-amino-alcohols using a variant of the Hofmann–Löffler–Freytag reaction to promote β selective C-H amination of ...
The reaction mechanism is that of the related Hofmann degradation. [2] Weermann degradation 1st unsattuered. At first the carbonic acid amide (1) reacts with the sodium hypochlorite. After separate water and chloride an amine with a free bond is built 2. The intermediate (3) is generated by rearrangement. At this point two different mechanisms ...
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]
Hofmann bromamide reaction; Hofmann degradation, Exhaustive methylation; Hofmann elimination; Hofmann Isonitrile synthesis, Carbylamine reaction; Hofmann product; Hofmann rearrangement; Hofmann–Löffler reaction, Löffler–Freytag reaction, Hofmann–Löffler–Freytag reaction; Hofmann–Martius rearrangement; Hofmann's rule; Hofmann–Sand ...
This organic reaction is closely related to the Hofmann elimination, but the base is a part of the leaving group. Sulfoxides can undergo an essentially identical reaction to produce sulfenic acids, which is important in the antioxidant chemistry of garlic and other alliums. Selenoxides likewise undergo selenoxide eliminations.
There are other processes of preparing an amide such as from acid anhydrides and acyl chloride. [2] Carboxylic acids react with ammonium carbonate, to convert the carboxylic acids to ammonium salts. For example, acetic acid reacts with ammonium carbonate to produce ammonium acetate. [3]
These possibilities have been used to account for the fact that, for certain substrates like α-tetralone, the group that migrates can sometimes change, depending on the conditions used, to deliver either of the two possible amides. [8] Two proposed reaction mechanisms for the amide formation from a ketone via Schmidt reaction