The special directing effect of fluorine: Ligand independent ortho lithiation of 1-(fluorophenyl)pyrroles

F. Faigl, Katalin Fogassy, Zoltán Szántó, Antal Lopata, L. Tőke

Research output: Contribution to journalArticle

11 Citations (Scopus)

Abstract

Lithiation of l-(fluorophenyl)pyrroles occurred exclusively ortho to the fluorine substituent independently of the structure of the tertiary amine type ligands use. Semiempirical quantum chemical calculations confirmed that the special directing effect of fluorine atom is manifested by increasing kinetic acidity of the neighbouring position while the α hydrogens of the pyrrole rings are the most acidic in ground state.

Original languageEnglish
Pages (from-to)4367-4374
Number of pages8
JournalTetrahedron
Volume54
Issue number17
DOIs
Publication statusPublished - Apr 23 1998

Fingerprint

Special effects
Pyrroles
Fluorine
Ligands
Acidity
Ground state
Amines
Hydrogen
Atoms
Kinetics

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

The special directing effect of fluorine : Ligand independent ortho lithiation of 1-(fluorophenyl)pyrroles. / Faigl, F.; Fogassy, Katalin; Szántó, Zoltán; Lopata, Antal; Tőke, L.

In: Tetrahedron, Vol. 54, No. 17, 23.04.1998, p. 4367-4374.

Research output: Contribution to journalArticle

Faigl, F. ; Fogassy, Katalin ; Szántó, Zoltán ; Lopata, Antal ; Tőke, L. / The special directing effect of fluorine : Ligand independent ortho lithiation of 1-(fluorophenyl)pyrroles. In: Tetrahedron. 1998 ; Vol. 54, No. 17. pp. 4367-4374.
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