Unexpected cleavage of upper rim-bridged calix[4]arenes leading to linear oligophenolic derivatives

被引：7
|
作者：
Slavik, P. [1 ]
Dvorakova, H. [2 ]
Krupicka, M. [1 ]
Lhotak, P. [1 ]
机构：
[1] Prague UCTP, Dept Organ Chem, Tech 5, Prague 16628 6, Czech Republic
[2] UCTP, Lab NMR Spect, Prague 16628 6, Czech Republic
来源：
ORGANIC & BIOMOLECULAR CHEMISTRY | 2018年 / 16卷 / 05期
关键词：
HARTREE-FOCK; BASIS-SETS; SUBSTITUTION; CALIXARENES;
D O I：
10.1039/c7ob03101g
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Regioselective meta-mercuration followed by Pd-catalysed intramolecular bridging gave birth to a novel type of calixarene bearing a single bond bridge between the meta positions of the neighboring aromatic subunits. These bridged derivatives possess extremely distorted cavities that imply possible amended properties over common calix[4]arenes. This new type of calixarene reactivity can be documented by acid-/electrophile-mediated cleavage of the basic macrocyclic skeleton leading to open oligomeric structures-the behavior of which has never been observed before in classic calix[4]arenes bearing alkoxy groups on the lower rim.
引用
收藏
页码：838 / 843
页数：6
相关论文
共 50 条
  • [21] Lower rim upper rim hydrogen-bonded adducts of calix[4]arenes
    Vreekamp, RH
    Verboom, W
    Reinhoudt, DN
    JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (13): : 4282 - 4288
  • [22] Photoresponsive lower-rim azobenzene substituted and bridged calix[4]arenes
    Vögtle, F
    Udelhofen, D
    Abramson, S
    Fuchs, B
    JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY A-CHEMISTRY, 2000, 131 (1-3) : 41 - 48
  • [23] Shaping of calix[4]arenes via double bridging of the upper rim
    Slavik, Petr
    Eigner, Vaclav
    Lhotak, Pavel
    CRYSTENGCOMM, 2016, 18 (26): : 4964 - 4970
  • [24] Synthesis and Properties of Upper Rim Schiff Base Calix[4]arenes
    Tie-Dong Guo
    Qi-Yu Zheng
    Lian-Ming Yang
    Zhi-Tang Huang
    Journal of inclusion phenomena and macrocyclic chemistry, 2000, 36 : 327 - 333
  • [25] Synthesis and properties of upper rim Schiff base calix[4]arenes
    Guo, TD
    Zheng, QY
    Yang, LM
    Huang, ZT
    JOURNAL OF INCLUSION PHENOMENA AND MACROCYCLIC CHEMISTRY, 2000, 36 (03) : 327 - 333
  • [26] Photoswitchable calix[4]arenes bearing dihydroacridine substituents at the upper rim
    Grubert, Lutz
    Abraham, Wemer
    TETRAHEDRON, 2007, 63 (44) : 10778 - 10787
  • [27] Complexation of upper rim phosphorylated calix[4]arenes with uracil derivatives in water-containing solution
    Kalchenko, O
    Marcinowicz, A
    Poznanski, J
    Cherenok, S
    Solovyov, A
    Zielenkiewicz, W
    Kalchenko, V
    JOURNAL OF PHYSICAL ORGANIC CHEMISTRY, 2005, 18 (07) : 578 - +
  • [28] Synthesis of potential receptor molecules by combination of upper-rim-functionalized calix[4]arenes and partly bridged resorcinarenes
    Timmerman, P.
    Boerrigter, H.
    Verboom, W.
    Reinhoudt, D. N.
    Recueil des Travaux Chimiques des Pays-Bas, 114 (03):
  • [29] SYNTHESIS OF POTENTIAL RECEPTOR MOLECULES BY COMBINATION OF UPPER-RIM-FUNCTIONALIZED CALIX[4]ARENES AND PARTLY BRIDGED RESORCINARENES
    TIMMERMAN, P
    BOERRIGTER, H
    VERBOOM, W
    REINHOUDT, DN
    RECUEIL DES TRAVAUX CHIMIQUES DES PAYS-BAS-JOURNAL OF THE ROYAL NETHERLANDS CHEMICAL SOCIETY, 1995, 114 (03): : 103 - 111
  • [30] Synthesis of upper rim-double-bridged calix[4]arenes bearing seven membered rings and related compounds
    Tlusty, M.
    Eigner, V.
    Babor, M.
    Kohout, M.
    Lhotak, P.
    RSC ADVANCES, 2019, 9 (38) : 22017 - 22030
12345