Az 1-(metoxi-fenil)pirrolok és az 1-(fluor-fenil)pirrolok regioszelektív lítiálása

Translated title of the contribution: Regioselective lithiation of 1-(methoxyphenyl)-pyrroles and 1-(fluorophenyl)pyrroles

Ferenc Faigl, Katalin Fogassy, Angelika Thurner, László Toke, Zoltán Szántó, Antal Lopata

Research output: Contribution to journalArticle

Abstract

Role of tertiary amine type two- and three-dentate ligands was studied in regioselective lithiations of 1-(methoxyphenyl)- and 1-(fluorophenyl)pyrroles with butyllithium (BuLi). In the presence of N,N,N′,N′- tetramethylethylenediamine lithiation occurred in ortho position to the methoxy group, while clean α-metallation of the pyrrole ring was observed when N,N,N′,N″,N″-pentamethyldiethylenetriamine was the activating ligand. In the series of 1-(fluorophenyl)pyrroles lithiation occurred in ortho position to the fluorine independently of the structure of the tertiary amine type ligands used. 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 ring are the most acidic in ground state.

Original languageHungarian
Pages (from-to)311-316
Number of pages6
JournalMagyar Kemiai Folyoirat, Kemiai Kozlemenyek
Volume108
Issue number7
Publication statusPublished - Jul 2002

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

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Az 1-(metoxi-fenil)pirrolok és az 1-(fluor-fenil)pirrolok regioszelektív lítiálása. / Faigl, Ferenc; Fogassy, Katalin; Thurner, Angelika; Toke, László; Szántó, Zoltán; Lopata, Antal.

In: Magyar Kemiai Folyoirat, Kemiai Kozlemenyek, Vol. 108, No. 7, 07.2002, p. 311-316.

Research output: Contribution to journalArticle

Faigl, Ferenc ; Fogassy, Katalin ; Thurner, Angelika ; Toke, László ; Szántó, Zoltán ; Lopata, Antal. / Az 1-(metoxi-fenil)pirrolok és az 1-(fluor-fenil)pirrolok regioszelektív lítiálása. In: Magyar Kemiai Folyoirat, Kemiai Kozlemenyek. 2002 ; Vol. 108, No. 7. pp. 311-316.
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AU - Szántó, Zoltán

AU - Lopata, Antal

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