User:Benjah-bmm27/degree/2/CPB
Appearance
![](http://upload.wikimedia.org/wikipedia/commons/thumb/2/24/N-acyl-N-%28leaving-group%29ylamide-anion-anion-rearrangement-mechanism-2D.png/500px-N-acyl-N-%28leaving-group%29ylamide-anion-anion-rearrangement-mechanism-2D.png)
Introduction[edit]
"Rearrangements involving Carbocationic or Polar Intermediates", Dr Craig Butts
Species[edit]
Stereoelectronic effects[edit]
- Stereoelectronic effects
- Inductive effect
- Mesomeric effect (e.g. allyl, benzyl C+)
- Hyperconjugation, Beta-silicon effect
- Non-classical ions: norbornyl carbocations
Mechanisms[edit]
- Synchronicity of mechanisms: stepwise reaction, concerted reaction, reaction intermediate,
- Rearrangement reaction
- 1,2-rearrangement
Pinacol[edit]
Tiffeneau-Demjanov[edit]
- Tiffeneau-Demjanov rearrangement
- Diazomethane variation
Wolff[edit]
Demjanov[edit]
Wagner-Meerwein[edit]
Arndt-Eistert[edit]
Corey-Fuchs[edit]
- Corey-Fuchs reaction
- converts aldehydes to alkynes, RCHO → RCCH
- a special case of the Wittig reaction with Ph3P=CBr2, forms RHC=CBr2, then BuLi and H2O to RCCH
Hoffman[edit]
Curtius, Lossen, Schmidt[edit]
Beckmann[edit]
Baeyer-Villiger[edit]
External links[edit]
- Animations of rearrangements from ChemTube 3d: http://www.chemtube3d.com/Rearrangements-Home.html
- Full notes: http://www.benjamin-mills.com/bristol/rearrangements/