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

Beilstein Journal of Organic Chemistry

Victor N. Nemykin¹  Thomas Wirth²  Pavel S. Postnikov³  Rosa Y. Yusubova³  Irina A. Mironova³  Akira Yoshimura³  Viktor V. Zhdankin³  Mekhman S. Yusubov³ 

[1] Department of Chemistry, University of Manitoba, Winnipeg, MB R3T 2N2, Canada;School of Chemistry, Cardiff University Park Place, Main Building, Cardiff CF10 3AT, UK;The Tomsk Polytechnic University, 634050 Tomsk, Russia;

关键词: hypervalent iodine;    iodine;    2-iodoxybenzenesulfonic acid;    oxidation;    X-ray;   

DOI  :  10.3762/bjoc.14.159

来源: DOAJ

【 摘 要 】

The selective preparation of 2-iodoxybenzenesulfonic acid (IBS, as potassium or sodium salts) by oxidation of sodium 2-iodobenzenesulfonate 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.

【 授权许可】

Unknown