Nitration of thiacalix[4]arene derivatives

被引：22
|
作者：
Lhoták, P
Svoboda, J
Stibor, I
Sykora, J
机构：
[1] Inst Chem Technol, Dept Organ Chem, CR-16628 Prague 6, Czech Republic
[2] Acad Sci Czech Republ, Inst Chem Proc Fundamentals, CR-16502 Prague, Czech Republic
来源：
TETRAHEDRON LETTERS | 2002年 / 43卷 / 41期
关键词：
D O I：
10.1016/S0040-4039(02)01667-2
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A direct nitration of the upper rim of thiacalix[4]arenes is not possible due to the undesirable oxidation of the sulphur atoms during the nitration step leading to very complicated reaction mixtures. On the other hand, thiacalix[4]arene derivatives can be at first transformed intentionally to the highest oxidation state-sulfones, and subsequently ipso-nitrated using 100% HNO3 in CF3COOH. This procedure gives smoothly mono- or dinitro-derivatives in acceptable yields which opens the way for further derivatisation of the upper rim of thiacalixarenes. (C) 2002 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码：7413 / 7417
页数：5
相关论文
共 50 条
  • [31] Synthesis and structure of lower rim-substituted alkynyl derivatives of thiacalix[4]arene
    A. A. Murav’ev
    F. B. Galieva
    A. G. Strel’nik
    R. I. Nugmanov
    M. Grüner
    S. E. Solov’eva
    Sh. K. Latypov
    I. S. Antipin
    A. I. Konovalov
    Russian Journal of Organic Chemistry, 2015, 51 : 1334 - 1342
  • [32] Pyridinyl hydrazone derivatives of thiacalix[4]arene as selective extractants of transition metal ions
    Sergey N. Podyachev
    Nadezda E. Burmakina
    Victor V. Syakaev
    Svetlana N. Sudakova
    Wolf D. Habicher
    Alexander I. Konovalov
    Journal of Inclusion Phenomena and Macrocyclic Chemistry, 2011, 71 : 161 - 168
  • [33] Pyridinyl hydrazone derivatives of thiacalix[4]arene as selective extractants of transition metal ions
    Podyachev, Sergey N.
    Burmakina, Nadezda E.
    Syakaev, Victor V.
    Sudakova, Svetlana N.
    Habicher, Wolf D.
    Konovalov, Alexander I.
    JOURNAL OF INCLUSION PHENOMENA AND MACROCYCLIC CHEMISTRY, 2011, 71 (1-2) : 161 - 168
  • [34] Unexpected cleavage of thiacalix[4]arene sulfoxides
    Miksatko, J.
    Eigner, V.
    Lhotak, P.
    RSC ADVANCES, 2017, 7 (84): : 53407 - 53414
  • [35] Upper rim substitution of thiacalix[4]arene
    Lhoták, P
    Himl, M
    Stibor, I
    Sykora, J
    Cisarová, I
    TETRAHEDRON LETTERS, 2001, 42 (40) : 7107 - 7110
  • [36] The Unexpected Chemistry of Thiacalix[4]arene Monosulfoxide
    Mamleev, Kamil
    Eigner, Vaclav
    Dvorakova, Hana
    Lhotak, Pavel
    MOLECULES, 2023, 28 (09):
  • [37] Synthesis of unique cagelike thiacalix[4]arene derivatives in a 1,3-alternate conformation
    St'astny, Vaclav
    Stibor, Ivan
    Cisarova, Ivana
    Sykora, Jan
    Pojarova, Michaela
    Lhotak, Pavel
    JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (14): : 5404 - 5406
  • [38] Thiacalix[4] arene derivatives as radium ionophores:: a study on the requirements for Ra2+ extraction
    van Leeuwen, FWB
    Beijleveld, H
    Velders, AH
    Huskens, J
    Verboom, W
    Reinhoudt, DN
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2005, 3 (10) : 1993 - 2001
  • [39] Selectivity of solid-contact Ag potentiometric sensors based on thiacalix[4]arene derivatives
    Evtugyn, G. A.
    Stoikov, I. I.
    Belyakova, S. V.
    Stoikova, E. E.
    Shamagsumova, R. V.
    Zhukov, A. Yu.
    Antipin, I. S.
    Budnikov, H. C.
    TALANTA, 2008, 76 (02) : 441 - 447
  • [40] Band intensity in the IR spectra and conformations of calix[4]arene and thiacalix[4]arene
    Furer, VL
    Borisoglebskaya, EI
    Kovalenko, VI
    SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY, 2005, 61 (1-2) : 355 - 359
12345