A [3,3]-sigmatropic rearrangement is a key step in the Fischer indole synthesis
Click the structures and reaction arrows in sequence to view the 3D models and animations respectively
The Fischer indole synthesis is a famous method of making biologically important indoles. A key step involves a [3,3]-sigmatropic rearrangement where the sigma bond that breaks is between two nitrogen atoms. The sigma bond that forms links two rings with a C-C bond.
Ionic reaction steps are not shown which constitute the remainder of the Fischer indole synthesis.
Richard Windsor - Undergraduate Final Year Project 2008