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

被引：16

作者：

Faigl, F ^{[1
]}

Fogassy, K

Szucs, E

Kovács, K

Keseru, GM

Harmat, V

Böcskei, Z

Toke, L

机构：

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

[2] Tech Univ Budapest, Dept Chem Informat Technol, H-1521 Budapest, Hungary

[3] Eotvos Lorand Univ, Dept Theoret Chem, H-1117 Budapest, Hungary

来源：

TETRAHEDRON | 1999年 / 55卷 / 25期

关键词：

lithiation; regiocontrol; aromaticity; X-ray crystal structures;

D O I：

10.1016/S0040-4020(99)00398-1

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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. (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

页码：7881 / 7892

页数：12

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