Unprecedented formation of lactone derivatives in thiacalix[4]arene series

被引:34
作者
Lhoták, P
Dudic, M
Stibor, I
Petrícková, H
Sykora, J
Hodacová, J
机构
[1] Inst Chem Technol, Dept Organ Chem, Technicka 5, Prague 16628 6, Czech Republic
[2] Inst Chem Technol, Dept Solid State Chem, Prague 16628 6, Czech Republic
[3] Acad Sci Czech Republ, Inst Organ Chem & Biochem, CR-16610 Prague 6, Czech Republic
关键词
D O I
10.1039/b100906k
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Distal bis(carboxymethyloxy) derivatives of thiacalix[4]arene were found to undergo an unprecedented intramolecular cyclisation to yield lactone compounds 5a or 5b, the structure of lactones possessing nine-membered ring was proved by X-ray crystallography; inherent chirality of new compounds was demonstrated using separation on a chiral HPLC column.
引用
收藏
页码:731 / 732
页数:2
相关论文
共 16 条
[1]   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
[2]   CALIXARENES, MACROCYCLES WITH (ALMOST) UNLIMITED POSSIBILITIES [J].
BOHMER, V .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1995, 34 (07) :713-745
[3]  
Gutsche C. D., 1998, CALIXARENES REVISITE, V6
[4]   Novel cavity design using calix[n]arene skeletons: Toward molecular recognition and metal binding [J].
Ikeda, A ;
Shinkai, S .
CHEMICAL REVIEWS, 1997, 97 (05) :1713-1734
[5]   Selective synthesis of three conformational isomers of tetrakis[(ethoxycarbonyl)methoxy]thiacalix[4]arene and their complexation properties towards alkali metal ions [J].
Iki, N ;
Narumi, F ;
Fujimoto, T ;
Morohashi, N ;
Miyano, S .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1998, (12) :2745-2750
[6]   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
[7]   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
[8]   Conformational flexibility of a novel tetraethylether of thiacalix[4]arene.: A comparison with the "classical" methylene-bridged compounds [J].
Lang, J ;
Dvoráková, H ;
Bartosová, I ;
Lhoták, P ;
Stibor, I ;
Hrabal, R .
TETRAHEDRON LETTERS, 1999, 40 (02) :373-376
[9]  
LANG J, IN PRESS J CHEM S P2
[10]   Tetraalkylated 2,8,14,20-tetrathiacalix [4] arenes:: Novel infinite channels in the solid state [J].
Lhoták, P ;
Himl, M ;
Pakhomova, S ;
Stibor, I .
TETRAHEDRON LETTERS, 1998, 39 (48) :8915-8918