Selectivity in radical alkylation of substituted pyrroles

The theoretical study of a highly regioselective intermolecular oxidative free‐radical substitution of 2‐ and 3‐formylpyrroles that yields 2,5‐ and 2,3‐disubstituted pyrroles, respectively, is described. A mechanistic and kinetic study was carried out using quantum chemical methods and classical tra...

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Bibliographic Details
Published in:International journal of quantum chemistry 2010-03, Vol.110 (3), p.697-705
Main Authors: Iuga, Cristina, Uribe, Simón Olguín, Miranda, Luis D., Vivier-Bunge, Annik
Format: Article
Language:English
Subjects:
radical alkylation
reaction kinetics
regioselectivity
substituted pyrroles
theoretical study
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Summary:The theoretical study of a highly regioselective intermolecular oxidative free‐radical substitution of 2‐ and 3‐formylpyrroles that yields 2,5‐ and 2,3‐disubstituted pyrroles, respectively, is described. A mechanistic and kinetic study was carried out using quantum chemical methods and classical transition state theory. Rate constants were obtained at 298 K and atmospheric pressure. All possible channels were considered and branching ratios were obtained. The selectivity predicted using theoretical methods agrees very‐well with experimental results. © 2009 Wiley Periodicals, Inc. Int J Quantum Chem, 2010
ISSN:0020-7608
1097-461X
DOI:10.1002/qua.22178