Pyrrole-Mannich-Electrophilic Substitution

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

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Pyrrole reacts with the iminium cation mainly at the 2- (or 5-) position but if these positions are blocked then the reaction will take place at the 3- and 4- positions.

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M. Arend, B. Westermann and N. Risch, Angew. Chemie Int. Ed., 1998, 37, 1044–1070.