Vilsmeier - Nucleophilic Substitution Tutorial

Tutorial and Self Assessment Available Pyrrole - Vilsmeier

Nucleophilic Substitution (Electrophilic substitution on pyrrole)

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NOTE: Important charges and non-bonding electrons are shown throughout the animation except during the transition phase

Click the structures and reaction arrows to view the 3D models and animations respectively

The iminium cation reacts with pyrrole to give a more stable iminium salt. The extra stability comes from the conjugation between the pyrrole nitrogen and the iminium group.

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J. Muzart, Tetrahedron, 2009, 65, 8313–8323.