Synthesis and NMR studies of 2-and 3-fluorosubstitued five-membered heterocycles

被引：21

作者：

Dvornikova, E

Bechcicka, M

Kamienska-Trela, K

Krówczynski, A

机构：

[1] Polish Acad Sci, Inst Organ Chem, PL-01224 Warsaw, Poland

[2] Univ Warsaw, Dept Chem, PL-02089 Warsaw, Poland

来源：

JOURNAL OF FLUORINE CHEMISTRY | 2003年 / 124卷 / 02期

关键词：

2-and 3-fluoro derivatives; thiophene; pyrrole; furan; (1)J(CC) couplings; DFT calculations;

D O I：

10.1016/j.jfluchem.2003.07.001

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

A set of 2-fluoro- and 3-fluoro-substituted thiophenes, pyrroles and furans has been synthesized by a treatment of the corresponding lithio derivatives with N-fluorodibenzenesulfonamide. For all these compounds, (1)J(CC) and (1)J(CH) coupling constants and F-19 NMR chemical shifts have been measured. In all cases, a dramatic increase of the (1)J(C2C3) couplings has been observed in 2-fluoro- and 3-fluoro-substituted compounds in comparison with those measured for the parent compounds. The same is valid for (1)JC(3)C(4) measured in 3-fluoro derivatives. The DFF calculations performed for 2- and 3-fluoro-substituted compounds reproduce very well the experimental coupling values and show that the Fermi contact contribution is the main factor determining their magnitude. Also the trends observed in the F-19 NMR shieldings are well reflected in the calculated DFF data. (C) 2003 Elsevier B.V. All rights reserved.

引用

页码：159 / 168

页数：10

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