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Wagner-Meerwein rearrangement

 

 
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Wagner-Meerwein rearrangement
 
 
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A Wagner-Meerwein rearrangement is a class of carbocation
Carbocation

A carbocation is an ion with a positively-charged carbon atom. The charged carbon atom in a carbocation is a "sextet", i.e. it has only six electrons in its outer Electron shell#Valence shell instead of the eight valence electrons that ensures maximum stability ....
 1,2-rearrangement
1,2-rearrangement

A 1,2-rearrangement or 1,2-migration or 1,2-shift or Frank C. Whitmore 1,2-shift is an organic reaction where a substituent moves from one atom to another atom in a chemical compound....
 reaction
Rearrangement reaction

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 ....
s in which a hydrogen
Hydrogen

Hydrogen is the chemical element with atomic number 1. It is represented by the chemical symbol H. At standard temperature and pressure, hydrogen is a colorless, odorless, nonmetallic, tasteless, highly combustion and explosive Diatomic molecule gas with the molecular formula H2....
, alkyl
Alkyl

An alkyl is a univalent Radical consisting of carbon and hydrogen atoms, arranged in a chain. The Alkyls form homologous series with the general formula CnH2n+1....
 or aryl
Aryl

In the context of organic molecules, aryl refers to any functional group or substituent derived from a simple aromatic ring, may it be phenyl, thiophene, indole, etc ....
 group migrates from one carbon to a neighboring carbon.

Several reviews have been published.

The rearrangement was first discovered in bicyclic terpene
Terpene

Terpenes are a large and varied class of hydrocarbons, produced primarily by a wide variety of plants, particularly conifers, though also by some insects such as termites or swallowtail butterflies, which emit terpenes from their osmeterium....
s for example the conversion of isoborneol to camphene
Camphene

Camphene is bicyclic terpene. It is nearly insoluble in water, but very soluble in common organic solvents. It volatilizes readily at room temperature and has a pungent smell....
 :


The story of the rearrangement reveals that many scientists were puzzled with this and related reactions and its close relationship to the discovery of carbocations as intermediates.

The related Nametkin rearrangement named after Sergey Namyotkin
Sergey Namyotkin

Sergey Semyonovich Namyotkin was a Russian chemist, a prominent researcher in terpene chemistry and rearrangement of camphenes ....
 involves the rearrangement of methyl groups in certain terpenes.






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A Wagner-Meerwein rearrangement is a class of carbocation
Carbocation

A carbocation is an ion with a positively-charged carbon atom. The charged carbon atom in a carbocation is a "sextet", i.e. it has only six electrons in its outer Electron shell#Valence shell instead of the eight valence electrons that ensures maximum stability ....
 1,2-rearrangement
1,2-rearrangement

A 1,2-rearrangement or 1,2-migration or 1,2-shift or Frank C. Whitmore 1,2-shift is an organic reaction where a substituent moves from one atom to another atom in a chemical compound....
 reaction
Rearrangement reaction

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 ....
s in which a hydrogen
Hydrogen

Hydrogen is the chemical element with atomic number 1. It is represented by the chemical symbol H. At standard temperature and pressure, hydrogen is a colorless, odorless, nonmetallic, tasteless, highly combustion and explosive Diatomic molecule gas with the molecular formula H2....
, alkyl
Alkyl

An alkyl is a univalent Radical consisting of carbon and hydrogen atoms, arranged in a chain. The Alkyls form homologous series with the general formula CnH2n+1....
 or aryl
Aryl

In the context of organic molecules, aryl refers to any functional group or substituent derived from a simple aromatic ring, may it be phenyl, thiophene, indole, etc ....
 group migrates from one carbon to a neighboring carbon.

Several reviews have been published.

The rearrangement was first discovered in bicyclic terpene
Terpene

Terpenes are a large and varied class of hydrocarbons, produced primarily by a wide variety of plants, particularly conifers, though also by some insects such as termites or swallowtail butterflies, which emit terpenes from their osmeterium....
s for example the conversion of isoborneol to camphene
Camphene

Camphene is bicyclic terpene. It is nearly insoluble in water, but very soluble in common organic solvents. It volatilizes readily at room temperature and has a pungent smell....
 :


The story of the rearrangement reveals that many scientists were puzzled with this and related reactions and its close relationship to the discovery of carbocations as intermediates.

The related Nametkin rearrangement named after Sergey Namyotkin
Sergey Namyotkin

Sergey Semyonovich Namyotkin was a Russian chemist, a prominent researcher in terpene chemistry and rearrangement of camphenes ....
 involves the rearrangement of methyl groups in certain terpenes. In some cases the reaction type is also called a retropinacol rearrangement (see Pinacol rearrangement
Pinacol rearrangement

The pinacol rearrangement or pinacol-pinacolone rearrangement is a method for converting a diol to a carbonyl compound in organic chemistry....
).

See also

  • Demjanov rearrangement
    Demjanov rearrangement

    The Demjanov rearrangement is the chemical reaction of primary amines with nitrous acid to give rearranged alcohols. Both ring enlargement or contraction can occur....
  • Pinacol rearrangement
    Pinacol rearrangement

    The pinacol rearrangement or pinacol-pinacolone rearrangement is a method for converting a diol to a carbonyl compound in organic chemistry....