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

F. Faigl, Katalin Fogassy, Erzsébet Szucs, Krisztina Kovács, György M. Keseru, V. Harmat, Zsolt Böcskei, L. Tőke

Research output: Contribution to journalArticle

20 Citations (Scopus)

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

Fingerprint

Pyrroles
Molecular Structure
Molecular structure
Carboxylation
Molecular modeling
X-Rays
Single crystals
Derivatives
X rays
Acids

Keywords

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

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Effect of a trifluoromethyl group on molecular structure : Competitive mono- and dilithiation of 1-[(trifluoromethyl)phenyl]pyrroles. / Faigl, F.; Fogassy, Katalin; Szucs, Erzsébet; Kovács, Krisztina; Keseru, György M.; Harmat, V.; Böcskei, Zsolt; Tőke, L.

In: Tetrahedron, Vol. 55, No. 25, 18.06.1999, p. 7881-7892.

Research output: Contribution to journalArticle

Faigl, F. ; Fogassy, Katalin ; Szucs, Erzsébet ; Kovács, Krisztina ; Keseru, György M. ; Harmat, V. ; Böcskei, Zsolt ; Tőke, L. / Effect of a trifluoromethyl group on molecular structure : Competitive mono- and dilithiation of 1-[(trifluoromethyl)phenyl]pyrroles. In: Tetrahedron. 1999 ; Vol. 55, No. 25. pp. 7881-7892.
@article{d1a11ccacb7f4e4db66f1b8c1c9b634f,
title = "Effect of a trifluoromethyl group on molecular structure: Competitive mono- and dilithiation of 1-[(trifluoromethyl)phenyl]pyrroles",
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.",
keywords = "Aromaticity, Lithiation, Regiocontrol, X-Ray crystal structures",
author = "F. Faigl and Katalin Fogassy and Erzs{\'e}bet Szucs and Krisztina Kov{\'a}cs and Keseru, {Gy{\"o}rgy M.} and V. Harmat and Zsolt B{\"o}cskei and L. Tőke",
year = "1999",
month = "6",
day = "18",
doi = "10.1016/S0040-4020(99)00398-1",
language = "English",
volume = "55",
pages = "7881--7892",
journal = "Tetrahedron",
issn = "0040-4020",
publisher = "Elsevier Limited",
number = "25",

}

TY - JOUR

T1 - Effect of a trifluoromethyl group on molecular structure

T2 - Competitive mono- and dilithiation of 1-[(trifluoromethyl)phenyl]pyrroles

AU - Faigl, F.

AU - Fogassy, Katalin

AU - Szucs, Erzsébet

AU - Kovács, Krisztina

AU - Keseru, György M.

AU - Harmat, V.

AU - Böcskei, Zsolt

AU - Tőke, L.

PY - 1999/6/18

Y1 - 1999/6/18

N2 - 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.

AB - 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.

KW - Aromaticity

KW - Lithiation

KW - Regiocontrol

KW - X-Ray crystal structures

UR - http://www.scopus.com/inward/record.url?scp=0033581003&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0033581003&partnerID=8YFLogxK

U2 - 10.1016/S0040-4020(99)00398-1

DO - 10.1016/S0040-4020(99)00398-1

M3 - Article

AN - SCOPUS:0033581003

VL - 55

SP - 7881

EP - 7892

JO - Tetrahedron

JF - Tetrahedron

SN - 0040-4020

IS - 25

ER -