Reactivity of Aromatic Heterocycles

Pyrrole decarboxylation

Pyrrole is protonated at the carbon, as the positive charge can be delocalised on to nitrogen by resonance. Decarboxylation is then aided by attack of water on the carboxylic acid group.

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Xueli Cheng, Jinhu Wang, Ke Tang, Yongjun Liu, Chengbu Liu, Decarboxylation of pyrrole-2-carboxylic acid: A DFT investigation, Chemical Physics Letters, Volume 496, Issues 1–3, 20 August 2010, Pages 36-41, ISSN 0009-2614, 10.1016/j.cplett.2010.07.052. (