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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. [1] [2]
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 organic chemistry, a rearrangement reaction is a broad class of organic reactions where the carbon skeleton of a molecule is rearranged to give a structural isomer of the original molecule. [1] Often a substituent moves from one atom to another atom in the same molecule, hence these reactions are usually intramolecular.
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 rearrangement is widely used in organic synthesis. It is symmetry-allowed when it is suprafacial on all components. The transition state of the molecule passes through a boat or chair like transition state. An example of the Cope rearrangement is the expansion of a cyclobutane ring to a cycloocta-1,5-diene ring:
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 Auwers synthesis is a series of organic reactions forming a flavonol from a coumarone.This reaction was first reported by Karl von Auwers in 1908. [1] [2] [3] [4 ...
For example, when 2-iodobutane is treated with alcoholic potassium hydroxide (KOH), but-2-ene is the major product and but-1-ene is the minor product. [ 1 ] More generally, Zaytsev's rule predicts that in an elimination reaction the most substituted product will be the most stable, and therefore the most favored.