Pyrrole-Vilsmeier-Formation of an iminium cation

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

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The amide reacts with POCl₃ which makes off with the amide oxygen atom and replaces it with chlorine. This reaction is only favourable because of the strong P-O bond which is formed. The product of this reaction is an iminium cation.

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