Search results
Results From The WOW.Com Content Network
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 Curtius rearrangement (or Curtius reaction or Curtius degradation), first defined by Theodor Curtius in 1885, is the thermal decomposition of an acyl azide to an isocyanate with loss of nitrogen gas.
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 Hofmann rearrangement is a decarbonylation reaction whereby an amide is converted to an amine by way of an isocyanate intermediate. It is usually carried out under strongly basic conditions. It is usually carried out under strongly basic conditions.
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 reaction; Homo rearrangement of steroids; Hooker reaction; Horner–Wadsworth–Emmons ...
In the Curtius rearrangement, sodium azide and an acyl chloride are combined to quantitatively generate the acyl azide intermediate, and the rest of the reaction takes place under neutral conditions.) The carboxylic acid Schmidt reaction starts with acylium ion 1 obtained from protonation and loss of water.
The Bergmann degradation begins with benzoylation at the alpha-group of a peptide and subsequent conversion to an acyl azide. [1] As in the Curtius rearrangement, the acyl azide, in the presence of benzyl alcohol and heat, rearranges to a highly reactive isocyanate intermediate, releasing nitrogen gas in the process. [1]
PIFA can be used to carry out the Hofmann rearrangement under mildly acidic conditions, [11] rather than the strongly basic conditions traditionally used. [ 12 ] [ 13 ] The Hofmann decarbonylation of an N -protected asparagine has been demonstrated with PIDA, providing a route to β-amino- L - alanine derivatives.