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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 .
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.
Hock rearrangement; 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
The formation of the quinoline product is influenced by the interaction of both steric and electronic effects.In a recent study, Sloop [8] investigated how substituents would influence the regioselectivity of the product as well as the rate of reaction during the rate-determining step in a modified Combes pathway, which produced trifluoromethylquinoline as the product.
In the Hofmann elimination, treatment of a quaternary ammonium iodide salt with silver oxide produces hydroxide ions, which act as a base and eliminate the tertiary amine to give an alkene. [ 11 ] In the Hofmann elimination, the least substituted alkene is typically favored due to intramolecular steric interactions.
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.
While the Barton reaction has not enjoyed the popularity or widespread use of many other organic reactions, together with the mechanistically similar Hofmann–Löffler reaction it represents one of the first examples of C-H activation chemistry, a field which is now the topic of much frontline research in industrial and academic chemistry circles.
A stirred BZ reaction mixture showing changes in color over time. The discovery of the phenomenon is credited to Boris Belousov.In 1951, while trying to find the non-organic analog to the Krebs cycle, he noted that in a mix of potassium bromate, cerium(IV) sulfate, malonic acid, and citric acid in dilute sulfuric acid, the ratio of concentration of the cerium(IV) and cerium(III) ions ...