Tetraalkylated 2,8,14,20-tetrathiacalix [4] arenes:: Novel infinite channels in the solid state

被引:81
作者
Lhoták, P
Himl, M
Pakhomova, S
Stibor, I
机构
[1] Inst Chem Technol, Dept Organ Chem, Prague 6, Czech Republic
[2] Inst Chem Technol, Dept Solid State Chem, Prague 6, Czech Republic
关键词
calixarenes; alkylation; X-ray crystal structure;
D O I
10.1016/S0040-4039(98)01950-9
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The synthesis of new tetraalkylated derivatives of 2,8,14,20-tetrathiacalix[4]arenes was achieved by the refluxing of thiacalixarenes in acetone or acetonitrile with the alkylation agent (R-I, R-Br) in the presence of K2CO3 or Cs2CO3. The structure of the tetraalkylated thiacalix[4]arenes was studied hy means of H-1 NMR experiments proving the 1.3-alternate conformation under measurement conditions (CDCl3, room temperature). The same conformation was established by X-ray analysis in the solid state where these derivatives create nice infinite channels. (C) 1998 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:8915 / 8918
页数:4
相关论文
共 15 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]  
[Anonymous], 1989, MONOGRAPHS SUPRAMOLE
[3]   CALIXARENES, MACROCYCLES WITH (ALMOST) UNLIMITED POSSIBILITIES [J].
BOHMER, V .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1995, 34 (07) :713-745
[4]   ALTERNATIVE METHODS OF MODIFYING THE CALIXARENE CONFORMATION - THE SYNTHESIS AND MOLECULAR-STRUCTURES OF TERT-BUTYLCALIX[4]ARENE METHYL-ETHER COMPLEXED WITH ALUMINUM ALKYL SPECIES [J].
BOTT, SG ;
COLEMAN, AW ;
ATWOOD, JL .
JOURNAL OF INCLUSION PHENOMENA, 1987, 5 (06) :747-758
[5]   'Soft' calixarenes - Structural aspects of calixarene allyl ethers and of thiacalixarene synthesis [J].
Delaigue, X ;
Harrowfield, JM ;
Hosseini, MW ;
Mocerino, M ;
Skelton, BW ;
White, AH .
AUSTRALIAN JOURNAL OF CHEMISTRY, 1998, 51 (02) :111-121
[6]   SYNTHESIS AND CRYSTALLOGRAPHIC STUDIES OF A CALIX[4]ARENE WITH A 1,3-ALTERNATE CONFORMATION [J].
FUJIMOTO, K ;
NISHIYAMA, N ;
TSUZUKI, H ;
SHINKAI, S .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1992, (04) :643-648
[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]   CALIX[N]ARENES - POWERFUL BUILDING-BLOCKS OF SUPRAMOLECULAR CHEMISTRY [J].
LHOTAK, P ;
SHINKAI, S .
JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN, 1995, 53 (11) :963-974
[9]  
SCHATZ R, 1995, LIEBIGS ANN, P1401
[10]   CALIXARENES .26. SELECTIVE ESTERIFICATION AND SELECTIVE ESTER CLEAVAGE OF CALIX[4]ARENES [J].
SEE, KA ;
FRONCZEK, FR ;
WATSON, WH ;
KASHYAP, RP ;
GUTSCHE, CD .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (26) :7256-7268