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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.
Mechanism proposed for Kumada coupling (L = Ligand, Ar = Aryl). In such cases, the mechanism generally involves reductive elimination of R-R' from L n MR(R') (L = spectator ligand). This intermediate L n MR(R') is formed in a two step process from a low valence precursor L n M. The oxidative addition of an organic halide (RX) to L n M gives L n ...
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 scope of the Corey-House synthesis is exceptionally broad, and a range of lithium diorganylcuprates (R 2 CuLi, R = 1°, 2°, or 3° alkyl, aryl, or alkenyl) and organyl (pseudo)halides (RX, R = methyl, benzylic, allylic, 1°, or cyclic 2° alkyl, aryl, or alkenyl and X = Br, I, OTs, or OTf; X = Cl is marginal) will undergo coupling as the nucleophilic and electrophilic coupling partners ...
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.
Example mechanism for alkyne zipper reaction. The 3-aminopropylamine anion attacks the same lesser-substituted carbon adjacent to the allene , removing a proton and catalyzing a similar process, where the electrons from the carbon-hydrogen bond move to form a triple-bond (an alkyne ).
Anti-Markovnikov rearrangement. This product distribution can be rationalized by assuming that loss of the hydroxy group in 1 gives the tertiary carbocation A, which rearranges to the seemingly less stable secondary carbocation B. Chlorine can approach this center from two faces leading to the observed mixture of isomers.