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.

Background Colour:

Sn2

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

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. (http://www.sciencedirect.com/science/article/pii/S000926141000984X)

 

 

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