Selective functionalization of methylene bridges of calix[6]arenes. Isolation and identification of stable conformers of methyl ether of p-tert-butylcalix[6]arene

被引：5

作者：

Arora, Shafali ^{[1
]}

Sharma, Shivali ^{[1
]}

Mithu, Venus S. ^{[1
]}

Hee-Lee, Chang ^{[2
]}

Singh, Kamaljit ^{[1
]}

机构：

[1] Guru Nanak Dev Univ, UGC Ctr Adv Study 1, Dept Chem, Amritsar 143005, Punjab, India

[2] Kangwoon Natl Univ, Dept Chem, Chunchon 200701, South Korea

来源：

CHEMICAL COMMUNICATIONS | 2015年 / 51卷 / 20期

基金：

新加坡国家研究基金会;

关键词：

TRANS-ALKYL SUBSTITUENTS; CONFORMATIONAL-ANALYSIS; MOLECULAR RECOGNITION; METAL-BINDING; CALIXARENES; DERIVATIVES; ROUTE;

D O I：

10.1039/c4cc10400e

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Direct disubstitution at the methylene bridges of p-tert-butylcalix[6] arenemethyl ether has been achieved for the first time using a lithiation-substitution protocol. Two stable conformers have been isolated using column chromatography, and their structures have been unambiguously confirmed from 1D, 2D and variable temperature NMR studies and single crystal X-ray structure analysis.

引用

页码：4227 / 4230

页数：4

共 38 条

[1] Spirodienone route for the stereoselective methylene functionalization of p-tert-butylcalix[4]arene
Agbaria, K
Biali, SE
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (50) : 12495 - 12503
[2] Conformational behaviour of methyl p-tert-butylcalix[6]arene ester: Interconversions among 1,2,3-alternate conformations
Ahn, S
Lee, JW
Chang, SK
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1996, (01): : 79 - 82
[3] Asfari Z., 2001, Calixarenes
[4] Stepwise synthesis and structural characterization of calix[4]- and calix[5]arenes bearing a functionalized arm on the methylene bridge.
Bergamaschi, M
Bigi, F
Lanfranchi, M
Maggi, R
Pastorio, A
Pellinghelli, MA
Peri, F
Porta, C
Sartori, G
[J]. TETRAHEDRON, 1997, 53 (38) : 13037 - 13052
[5] Alkanediyl bridged calix[4]arenes: Synthesis, conformational analysis, and rotational barriers
Biali, SE
Bohmer, V
Cohen, S
Ferguson, G
Gruttner, C
Grynszpan, F
Paulus, EF
Thondorf, I
Vogt, W
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (51) : 12938 - 12949
[6] BIALI SE, 2003, SYNLETT, V1
[7] Bohmer V., 1997, LIEBIGS ANN RECL
[8] CASNATI A, 1992, ISRAEL J CHEM, V32, P79
[9] CHAWLA HM, 1995, TETRAHEDRON, V51, P2709
[10] Calix[4]arene derivatives monosubstituted at all four methylene bridges
Columbus, Ishay
Biali, Silvio E.
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2008, 73 (07) : 2598 - 2606

← 1 2 3 4 →