Synthesis and 1H NMR complexation study of thiacalix[4]arene tetraacetates

被引:56
作者
Lhoták, P
Stastny, V
Zlatusková, P
Stibor, I
Michlová, V
Tkadlecová, M
Havlícek, J
Sykora, J
机构
[1] Prague Inst Chem Technol, Dept Organ Chem, CR-16628 Prague 6, Czech Republic
[2] Prague Inst Chem Technol, Dept Analyt Chem, CR-16628 Prague 6, Czech Republic
[3] Prague Inst Chem Technol, Dept Solid State Chem, CR-16628 Prague 6, Czech Republic
关键词
calixarenes; thiacalixarenes; alkylation; NMR spectroscopy; X-ray diffraction; complexation; alkali metal cations;
D O I
10.1135/cccc20000757
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Alkylation of thiacalix[4]arenes with ethyl bromoacetate led to high yields (approximate to 60%) of corresponding tetraacetates in various conformations (cone, partial cone, 1,3-alternate) depending strictly on the carbonate (Na, K, Cs) used for the reaction. The complexation ability of new compounds was studied by H-1 NMR.
引用
收藏
页码:757 / 771
页数:15
相关论文
共 25 条
[1]   Thiacalixarenes:: Synthesis and structural analysis of thiacalix[4]arene and of p-tert-butylthiacalix[4]arene [J].
Akdas, H ;
Bringel, L ;
Graf, E ;
Hosseini, MW ;
Mislin, G ;
Pansanel, J ;
De Cian, A ;
Fischer, J .
TETRAHEDRON LETTERS, 1998, 39 (16) :2311-2314
[2]   Synthesis and solid state structural analysis of conformers of tetrakis((ethoxycarbonyl)methoxy)tetrathiacalix[4]arene [J].
Akdas, H ;
Mislin, G ;
Graf, E ;
Hosseini, MW ;
De Cian, A ;
Fischer, J .
TETRAHEDRON LETTERS, 1999, 40 (11) :2113-2116
[3]   SIR92 - a program for automatic solution of crystal structures by direct methods [J].
ALTOMARE, A ;
CASCARANO, G ;
GIACOVAZZO, G ;
GUAGLIARDI, A ;
BURLA, MC ;
POLIDORI, G ;
CAMALLI, M .
JOURNAL OF APPLIED CRYSTALLOGRAPHY, 1994, 27 :435-435
[4]   CALIXARENES, MACROCYCLES WITH (ALMOST) UNLIMITED POSSIBILITIES [J].
BOHMER, V .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1995, 34 (07) :713-745
[5]  
Gutsche C. D., 1989, CALIXARENES MONOGRAP, V1
[6]   High complexation ability of thiacalixarene with transition metal ions. The effects of replacing methylene bridges of tetra(p-t-butyl)calix[4]arenetetrol by epithio groups [J].
Iki, N ;
Morohashi, N ;
Narumi, F ;
Miyano, S .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1998, 71 (07) :1597-1603
[7]   A new chiral stationary phase for gas chromatography by use of a chiral thiacalix[4]arene derivative [J].
Iki, N ;
Narumi, F ;
Suzuki, T ;
Sugawara, A ;
Miyano, S .
CHEMISTRY LETTERS, 1998, (10) :1065-1066
[8]   Selective oxidation of thiacalix[4]arenes to the sulfinyl- and sulfonylcalix[4]arenes and their coordination ability to metal ions [J].
Iki, N ;
Kumagai, H ;
Morohashi, N ;
Ejima, K ;
Hasegawa, M ;
Miyanari, S ;
Miyano, S .
TETRAHEDRON LETTERS, 1998, 39 (41) :7559-7562
[9]   SYNTHESES AND ION SELECTIVITY OF ALL CONFORMATIONAL ISOMERS OF TETRAKIS((ETHOXYCARBONYL)METHOXY)CALIX[4]ARENE [J].
IWAMOTO, K ;
SHINKAI, S .
JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (26) :7066-7073
[10]   Facile synthesis of p-tert-butylthiacalix[4]arene by the reaction of p-tert-butylphenol with elemental sulfur in the presence of a base [J].
Kumagai, H ;
Hasegawa, M ;
Miyanari, S ;
Sugawa, Y ;
Sato, Y ;
Hori, T ;
Ueda, S ;
Kamiyama, H ;
Miyano, S .
TETRAHEDRON LETTERS, 1997, 38 (22) :3971-3972