TY - JOUR A1 - Mironova, Irina A. A1 - Postnikov, Pavel S. A1 - Yusubova, Rosa Y. A1 - Yoshimura, Akira A1 - Wirth, Thomas A1 - Zhdankin, Viktor V. A1 - Nemykin, Victor N. A1 - Yusubov, Mekhman S. T1 - Preparation and X-ray structure of 2-iodoxybenzenesulfonic acid (IBS) – a powerful hypervalent iodine(V) oxidant JF - Beilstein Journal of Organic Chemistry PY - 2018/// VL - 14 SP - 1854 EP - 1858 SN - 1860-5397 DO - 10.3762/bjoc.14.159 PB - Beilstein-Institut JA - Beilstein J. Org. Chem. UR - https://doi.org/10.3762/bjoc.14.159 KW - hypervalent iodine KW - iodine KW - 2-iodoxybenzenesulfonic acid KW - oxidation KW - X-ray N2 - 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. ER -