Preparation and X-ray structure of 2-iodoxybenzenesulfonic acid (IBS) – A powerful hypervalent iodine(V) oxidant

Irina A. Mironova, Pavel S. Postnikov, Rosa Y. Yusubova, Akira Yoshimura, Thomas Wirth, Viktor V. Zhdankin, Victor N. Nemykin, Mekhman S. Yusubov

Research output: Contribution to journalArticlepeer-review

7 Scopus citations

Abstract

The selective preparation of 2-iodoxybenzenesulfonic acid (IBS, as potassium or sodium salts) by oxidation of sodium 2-iodoben-zenesulfonate with Oxone or sodium periodate in water is reported. The single crystal X-ray diffraction analysis reveals a complex polymeric structure consisting of three units of IBS as potassium salt and one unit of 2-iodoxybenzenesulfonic acid linked together by relatively strong I=O···I intermolecular interactions. Furthermore, a new method for the preparation of the reduced form of IBS, 2-iodosylbenzenesulfonic acid, by using periodic acid as an oxidant, has been developed. It has been demonstrated that the oxidation of free 2-iodobenzenesulfonic acid under acidic conditions affords an iodine(III) heterocycle (2-iodosylbenzenesulfonic acid), while the oxidation of sodium 2-iodobenzenesulfonate in neutral aqueous solution gives the iodine(V) products.

Original languageEnglish (US)
Pages (from-to)1854-1858
Number of pages5
JournalBeilstein Journal of Organic Chemistry
Volume14
DOIs
StatePublished - Jul 20 2018

Bibliographical note

Funding Information:
This work was supported by the grant of the Russian Science Foundation (№ 16-13-10081), the grant of the Tomsk Polytechnic University Competitiveness Enhancement Program (VIU-195/2018), the National Science Foundation (CHE-1759798) and the Royal Society (IE160304).

Publisher Copyright:
© 2018 Mironova et al.

Keywords

  • 2-iodoxybenzenesulfonic acid
  • Hypervalent iodine
  • Iodine
  • Oxidation
  • X-ray

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