Regioselective substituent effects upon the synthesis of dipyrrins from 2-formyl pyrroles
CANADIAN JOURNAL OF CHEMISTRY(2018)
Abstract
The synthesis of symmetric a-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.
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Key words
dipyrrins,pyrroles,steric effects,condensation,synthesis
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