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

被引：10

作者：

Faigl, F ^{[1
]}

Fogassy, K

Szánto, Z

Lopata, A

Toke, L

机构：

[1] Tech Univ Budapest, Dept Organ Chem Technol, H-1521 Budapest, Hungary

[2] CheMicro Ltd, H-1108 Budapest, Hungary

[3] Hungarian Acad Sci, Organ Chem Technol Res Grp, H-1521 Budapest, Hungary

来源：

TETRAHEDRON | 1998年 / 54卷 / 17期

基金：

匈牙利科学研究基金会; 新加坡国家研究基金会;

关键词：

D O I：

10.1016/S0040-4020(98)00150-1

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Lithiation of 1-(fluorophenyl)pyrroles occurred exclusively ortho to the fluorine substituent 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 a hydrogens of the pyrrole rings are the most acidic in ground state. (C) 1998 Elsevier Science Ltd. All rights reserved.

引用

页码：4367 / 4374

页数：8

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