59435-13-1Relevant academic research and scientific papers
Regioselective substituent effects upon the synthesis of dipyrrins from 2-formyl pyrroles
Beh, Michael H.R.,Figliola, Carlotta,Lund, Kate-Lyn A.R.,Kajetanowicz, Aleksandra K.,Johnsen, Ann E.,Aronitz, Elise M.,Thompson, Alison
supporting information, p. 779 - 784 (2018/07/06)
The synthesis of symmetric α-free meso-H-dipyrrin hydrobromides from 5-H-2-formyl pyrroles was investigated. The self-condensation produces regioisomeric dipyrrins through adoption of two mechanistic pathways. The key difference between the two pathways lies in which position of the pyrrole directs nucleophilic attack. Through a systematic study involving various substituted and (or) isotopically labelled 5-H-2-formyl pyrroles, we herein provide evidence to suggest that not only do two mechanistic pathways exist, but the steric bulk of the substituent adjacent to the 5-unsubstituted position influences which pathway dominates.
