Introduction
edit"Rearrangements involving Carbocationic or Polar Intermediates", Dr Craig Butts
Species
editStereoelectronic 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
editTiffeneau-Demjanov
edit- Tiffeneau-Demjanov rearrangement
- Diazomethane variation
Wolff
editDemjanov
editWagner-Meerwein
editArndt-Eistert
editCorey-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
editCurtius, Lossen, Schmidt
editBeckmann
editBaeyer-Villiger
editExternal links
edit- Animations of rearrangements from ChemTube 3d: http://www.chemtube3d.com/Rearrangements-Home.html
- Full notes: http://www.benjamin-mills.com/bristol/rearrangements/