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/