Competition and co-operation between ortho directing groups and activating agents: Regioselective metallation of 1-(methoxyphenyl)pyrroles

被引：30

作者：

Faigl, F

Fogassy, K

Thurner, A

Toke, L

机构：

[1] Dept. of Organic Chemical Technology, Technical University of Budapest, Budapest

来源：

TETRAHEDRON | 1997年 / 53卷 / 13期

关键词：

D O I：

10.1016/S0040-4020(97)00183-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The role of di- and tri-dentate tertiary amine type ligands was studied in regioselective lithiation reactions of 1-(methoxyphenyl)pyrroles with butyllithium (LIC). Clean alpha-metallation of the pyrrole ring occured when N,N,N',N',N''-pentamethyldiethylenetriamine (PMDTA) was used 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.

引用

页码：4883 / 4888

页数：6

共 20 条

[1] MECHANISTIC EVIDENCE FOR ORTHO-DIRECTED LITHIATIONS FROM ONE-DIMENSIONAL AND TWO-DIMENSIONAL NMR-SPECTROSCOPY AND MNDO CALCULATIONS [J].