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The Beckmann rearrangement, named after the German chemist Ernst Otto Beckmann (1853–1923), is a rearrangement of an oxime functional group to substituted amides. [ 1 ] [ 2 ] The rearrangement has also been successfully performed on haloimines and nitrones .
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.
2.1 Beckmann rearrangement. 2.2 Schmidt reaction. 2.3 Cyclization of amino acids. 2.4 Intramolecular nucleophilic substitution. 2.5 Iodolactamization. 2.6 Kinugasa ...
The Claisen rearrangement is a powerful carbon–carbon bond-forming chemical reaction discovered by Rainer Ludwig Claisen. [1] The heating of an allyl vinyl ether will initiate a [3,3]-sigmatropic rearrangement to give a γ,δ-unsaturated carbonyl, driven by exergonically favored carbonyl CO bond formation Δ(Δ f H) = −327 kcal/mol (−1,370 kJ/mol).
One of the alkyl or aryl groups migrates from carbon to nitrogen with loss of nitrogen to give a nitrilium intermediate 6, as in the Beckmann rearrangement. Attack by water converts 6 to protonated imidic acid 7, which undergoes loss of proton to arrive at the imidic acid tautomer of the final amide.
The Bischler–Napieralski reaction is an intramolecular electrophilic aromatic substitution reaction that allows for the cyclization of β-arylethylamides or β-arylethylcarbamates.
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He was a teacher and organic chemist with a major interest in pharmaceutical and medicinal chemistry. He is known for the Stieglitz rearrangement, a rearrangement reaction in organic chemistry which commonly involves the formation of imines from hydroxylamines through a carbon to nitrogen shift, comparable to the key step of a Beckmann ...