Effect of a trifluoromethyl group on molecular structure: Competitive mono- and dilithiation of 1-[(trifluoromethyl)phenyl]pyrroles

Ferenc Faigl, Katalin Fogassy, Erzsébet Szucs, Krisztina Kovács, György M. Keseru, Veronika Harmat, Zsolt Böcskei, László Toke

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Abstract

Depending on the conditions used during the lithiation and subsequent carboxylation of 1-[(trifluoromethyl)phenyl]pyrroles the mono- and the dicarboxylated derivatives were selectively prepared. The regioselective formation of the monocarboxylic acids could be rationalized in the light of the data collected from the literature. Explanation of the other phenomena, such as regioselective dilithiation and the strong effect of the trifluoromethyl group on the structure and aromaticity of the pyrrole ring in the ortho position, has been elucidated by the aid of molecular modelling and single crystal X-Ray measurements.

Original languageEnglish
Pages (from-to)7881-7892
Number of pages12
JournalTetrahedron
Volume55
Issue number25
DOIs
Publication statusPublished - Jun 18 1999

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Keywords

  • Aromaticity
  • Lithiation
  • Regiocontrol
  • X-Ray crystal structures

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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