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A Wagner–Meerwein rearrangement is a class of carbocation 1,2-rearrangement reactions in which a hydrogen, alkyl or aryl group migrates from one carbon to a neighboring carbon. [ 1 ] [ 2 ] They can be described as cationic [1,2]- sigmatropic rearrangements, proceeding suprafacially and with stereochemical retention.
The cationic rearrangement contraction proceeds through the loss of a leaving group and the migration of an endocyclic bond to the carbocation. Pinacol type rearrangements are often used for this type of contraction. [20] Like the expansion reaction this proceeds with an electron donating group aiding in the migration.
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 1,2-rearrangement belongs to a broad class of chemical reactions called rearrangement reactions. A rearrangement involving a hydrogen atom is called a 1,2-hydride shift . If the substituent being rearranged is an alkyl group, it is named according to the alkyl group's anion : i.e. 1,2-methanide shift , 1,2-ethanide shift , etc.
This displacement can occur via a rearrangement (path A), in which one of the sigma bonds adjacent to the diazo group migrates. This migration results in an expansion of the ring. The resulting carbocation is then attacked by a molecule of water. Alternately, the diazo group can be displaced directly by a molecule of water in an S N 2 reaction ...
Carbocations are not formed in this process and thus rearrangements are not observed. The reaction follows Markovnikov's rule (the hydroxy group will always be added to the more substituted carbon). The oxymercuration part of the reaction involves anti addition of OH group but the demercuration part of the reaction involves free radical ...
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The Fowler process is typically done in two stages, the first stage being fluorination of cobalt(II) fluoride to cobalt(III) fluoride.. 2 CoF 2 + F 2 → 2 CoF 3. During the second stage, in this instance to make perfluorohexane, the hydrocarbon feed is introduced and is fluorinated by the cobalt(III) fluoride, which is converted back to cobalt(II) fluoride for reuse.