COMPETITION AND COOPERATION BETWEEN ORTHO DIRECTING GROUPS AND ACTIVATING AGENTS - REGIOSELECTIVE METALATION OF 1-(METHOXYPHENYL)PYRROLES

Authors
FAIGL F FOGASSY K THURNER A TOKE L
Citation
F. Faigl et al., COMPETITION AND COOPERATION BETWEEN ORTHO DIRECTING GROUPS AND ACTIVATING AGENTS - REGIOSELECTIVE METALATION OF 1-(METHOXYPHENYL)PYRROLES, Tetrahedron, 53(13), 1997, pp. 4883-4888
Citations number
20
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
53
Issue
13
Year of publication
1997
Pages
4883 - 4888
Database
ISI
SICI code
0040-4020(1997)53:13<4883:CACBOD>2.0.ZU;2-H
Abstract
The role of di- and tri-dentate tertiary amine type ligands was studie d in regioselective lithiation reactions of 1-(methoxyphenyl)pyrroles with butyllithium (LIC). Clean alpha-metallation of the pyrrole ring o ccured when N,N,N',N',N''-pentamethyldiethylenetriamine (PMDTA) was us ed while the benzene ring was lithiated ortho position to the methoxy group in the presence of N,N,N',N'-tetramethylethylenediamine (TMEDA). (C) 1997 Elsevier Science Ltd.