Mercuration of thiacalix[4]arenes in the cone and 1,3-alternate conformations

被引：5

作者：

Botha, F. ^{[1
]}

Boehm, S. ^{[1
]}

Dvorakova, H. ^{[2
]}

Eigner, V. ^{[3
,4
]}

Lhotak, P. ^{[1
]}

机构：

[1] Inst Chem Technol, Dept Organ Chem, CR-16628 Prague 6, Czech Republic

[2] Inst Chem Technol, Lab NMR Spect, CR-16628 Prague 6, Czech Republic

[3] Inst Chem Technol, Dept Solid State Chem, CR-16628 Prague 6, Czech Republic

[4] Inst Phys AS CR, Vvi, Prague 18221 8, Czech Republic

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2014年 / 12卷 / 28期

关键词：

UNCOMMON REGIOSELECTIVITY; S-ALKYLATION; META; THIACALIXARENES; SUBSTITUTION; SULFUR;

D O I：

10.1039/c4ob00799a

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The first mercuration in the thiacalixarene series using thiacalix[4] arenes immobilized in the cone or 1,3-alternate conformations gave a mixture of two monomercurated regioisomers (meta and para) in approx. 4 : 1 and 2 : 1 ratios, respectively. The organomercurial intermediates show unusual solid-state behaviour, as evidenced by the formation of. 6 complexes, and can be easily transformed into halogen-substituted derivatives, so far inaccessible in thiacalixarene chemistry. This paves the way towards the synthesis of inherently chiral thiacalixarene-based receptors with an unusual substitution pattern.

引用

页码：5136 / 5143

页数：8

共 50 条

[31] Chiral anion recognition by a ureido-thiacalix[4]arene ligand immobilized in the 1,3-alternate conformation
Mackova, Michaela
Miksatko, Jiri
Budka, Jan
Eigner, Vaclav
Curinova, Petra
Lhotak, Pavel
NEW JOURNAL OF CHEMISTRY, 2015, 39 (02) : 1382 - 1389
[32] Conformational rigidity in mesitylene-based calix[4]arenes adopting a 1,3-alternate conformation
Parzuchowski, P
Böhmer, V
Biali, SE
Thondorf, I
TETRAHEDRON-ASYMMETRY, 2000, 11 (11) : 2393 - 2402
[33] A fast access to non-symmetrically substituted 1,3-alternate conformers of calix[4]arenes
Kleij, AW
Prados, P
de Mendoza, J
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2004, 2004 (13) : 2848 - 2852
[34] Synthesis of multivalent oxamate ligands based on calix[4]arene and thiacalix[4]arene backbones in 1,3-Alternate conformation
Noamane, Mohamed Habib
Ferlay, Sylvie
Abidi, Rym
Hosseini, Mir Wais
TETRAHEDRON, 2017, 73 (30) : 4259 - 4264
[35] Unusual Reactivity of Aliphatic and Aromatic Amines with Bromoalkyl Derivatives of Thiacalix[4]arene in 1,3-Alternate Stereoisomeric Form
Burilov, Vladimir A.
Ibragimova, Regina R.
Gafiatullin, Bulat H.
Nugmanov, Ramil I.
Solovieva, Svetlana E.
Antipin, Igor S.
MACROHETEROCYCLES, 2017, 10 (02): : 215 - 220
[36] Cesium ion-selective electrodes based on 1,3-alternate thiacalix[4]biscrown-6,6
Choi, Y
Kim, H
Lee, JK
Lee, SH
Lim, HB
Kim, JS
TALANTA, 2004, 64 (04) : 975 - 980
[37] Rhodamine appended thiacalix[4]arene of 1,3-alternate conformation for nanomolar detection of Hg2+ ions
Kumar, Manoj
Kumar, Naresh
Bhalla, Vandana
SENSORS AND ACTUATORS B-CHEMICAL, 2012, 161 (01): : 311 - 316
[38] Conversion of 1,3-alternate to partial cone conformation of tetra-substituted calix[4]arene
Kang, SO
Nam, KC
BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 2000, 21 (02) : 167 - 168
[39] Influence of Nature of Functional Groups on Interaction of Tetrasubstituted at Lower Rim p-tert-Butyl Thiacalix[4]arenes in 1,3-Alternate Configuration with Model Lipid Membranes
D. A. Fayzullin
N. N. Vylegzhanina
O. I. Gnezdilov
V. V. Salnikov
A. V. Galukhin
I. I. Stoikov
I. S. Antipin
Yu. F. Zuev
Applied Magnetic Resonance, 2011, 40 : 231 - 243
[40] Influence of Nature of Functional Groups on Interaction of Tetrasubstituted at Lower Rim p-tert-Butyl Thiacalix[4]arenes in 1,3-Alternate Configuration with Model Lipid Membranes
Fayzullin, D. A.
Vylegzhanina, N. N.
Gnezdilov, O. I.
Salnikov, V. V.
Galukhin, A. V.
Stoikov, I. I.
Antipin, I. S.
Zuev, Yu. F.
APPLIED MAGNETIC RESONANCE, 2011, 40 (02) : 231 - 243

← 1 2 3 4 5 →