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RESEARCH ARTICLE
Contents Vol 75(9)

Halogenation of calix[4]arenes by [I(py)2]I3·2I2†

Peter Hahn A , Till Köhler A , Martin Börner A and Berthold Kersting https://orcid.org/0000-0001-5386-2809 A *
+ Author Affiliations
- Author Affiliations

A Institut für Anorganische Chemie, Universität Leipzig, Johannisallee 29, D-04103 Leipzig, Germany.

* Correspondence to: b.kersting@uni-leipzig.de

Handling Editor: George Koutsantonis

Australian Journal of Chemistry 75(9) 780-785 https://doi.org/10.1071/CH22031
Submitted: 8 February 2022  Accepted: 6 April 2022   Published: 26 May 2022

© 2022 The Author(s) (or their employer(s)). Published by CSIRO Publishing.

Abstract

The iodination of calix[4]arene and one of its monofunctionalised derivatives by bis(pyridine)iodonium(I) triiodide, [I(py)2]I3·2I2 has been studied. The iodination reactions proceed in good yields at room temperature (r.t.) without any co-reagents affording the corresponding tetra- and tri-substituted calix[4]arenes. Only electron-rich phenol groups are iodinated by [I(py)2]I3·2I2. Phenolether or Schiff-base type arene rings remain unaffected. The crystal structure of the iodination reagent, first published in 1961, has been re-determined which a higher precision. The crystal structures of the two per-iodinated calix[4]arenes show that self-inclusion occurs in the solid state.

Keywords: bis(pyridinium)iodonium triiodide, calixarenes, coordination chemistry: structures, hypervalent compounds, iodine, polyhalides, Schiff base, selective iodination reagent, self‐inclusion.


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