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Issue 28, 2014
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Mercuration of thiacalix[4]arenes in the cone and 1,3-alternate conformations

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Abstract

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 η6 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.

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

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Publication details

The article was received on 17 Apr 2014, accepted on 16 May 2014 and first published on 16 May 2014


Article type: Paper
DOI: 10.1039/C4OB00799A
Org. Biomol. Chem., 2014,12, 5136-5143

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

    F. Botha, S. Böhm, H. Dvořáková, V. Eigner and P. Lhoták, Org. Biomol. Chem., 2014, 12, 5136
    DOI: 10.1039/C4OB00799A

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