Mercuration of calix[4]arenes immobilized in the 1,2- and 1,3-alternate conformations

Petr Slavík, Václav Eigner, Stanislav Böhm, Pavel Lhoták*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review


Calix[4]arenes immobilized in the 1,2-alternate and 1,3-alternate conformations were directly mercurated using Hg(TFA)2. The reaction regioselectivity was compared with the thermodynamic stability of the corresponding products obtained by theoretical calculations (wB97XD/def2tzvp method). Both experimental and theoretical data suggest that para substitution is slightly preferred over meta attack for the 1,2-alternate conformer, while in the case of the 1,3-alternate conformation the situation is reversed. The usefulness of the mercury intermediates was demonstrated by the synthesis of a rigid upper-rim-bridged calixarene in the 1,2-alternate conformation possessing a highly distorted cavity. A simple transformation of the organomercury compounds afforded the corresponding iodo derivatives, which are potentially applicable as building blocks for further synthesis. Moreover, many products are inherently chiral representing unique substitution patterns inaccessible by common “mercury-free” chemistry.

Original languageEnglish
Pages (from-to)1846-1850
Number of pages5
JournalTetrahedron Letters
Issue number19
Early online date2 Apr 2017
Publication statusPublished - 10 May 2017


  • Bridgíng
  • Calix[4]arene
  • Mercuration
  • Regioselectivity

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