Synthesis of a deep-cavity thiacalix[4]arene

被引：32
作者：
Lhoták, P
Smejkal, T
Stibor, I
Havlícek, J
Tkadlecová, M
Petricková, H
机构：
[1] Inst Chem Technol, Dept Organ Chem, CR-16628 Prague 6, Czech Republic
[2] Inst Chem Technol, Dept Analyt Chem, CR-16628 Prague 6, Czech Republic
[3] Inst Chem Technol, Dept Solid State Chem, Prague 16628 6, Czech Republic
来源：
TETRAHEDRON LETTERS | 2003年 / 44卷 / 44期
关键词：
thiacalixarenes; X-ray crystallography; alkylation; conformational analysis;
D O I：
10.1016/j.tetlet.2003.09.048
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A novel thiacalix[4]arene derivative bearing four phenyl groups on the upper rim was prepared by the direct condensation of biphenyl-4-ol with elemental sulphur. As revealed by X-ray diffraction analysis, this compound adopts the cone conformation in the solid state, thus creating a cavity with an extended pi-aromatic system potentially applicable for solid-state inclusion of suitable molecules. Subsequent alkylation (RI/K2CO3/acetone, R=Me, Et, Pr) yielded tetraalkylated derivatives, which were studied for their conformational preferences using H-1 NMR spectroscopy. While the Me or Et derivatives are conformationally mobile and exhibit thermodynamic equilibria of several conformers in solution (CDCl3 or CD2Cl2) the corresponding propoxy derivative is infinitely stable at room temperature. (C) 2003 Elsevier Ltd. All rights reserved.
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收藏
页码：8093 / 8097
页数：5
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