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

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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
Pages (from-to)1854-1858
Number of pages5
JournalBeilstein Journal of Organic Chemistry
Volume14
DOIs
Publication statusPublished - 20 Jul 2018

Keywords

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

ASJC Scopus subject areas

  • Organic Chemistry

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