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

Mironova, Irina A., Postnikov, Pavel S., Yusubova, Rosa Y., Yoshimura, Akira, Wirth, Thomas, Zhdankin, Viktor V., Nemykin, Victor N. and Yusubov, Mekhman S. 2018. Preparation and X-ray structure of 2-iodoxybenzenesulfonic acid (IBS) - a powerful hypervalent iodine(V) oxidant. Beilstein Journal of Organic Chemistry 14 , pp. 1854-1858. 10.3762/bjoc.14.159

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Abstract

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.

Item Type: Article
Date Type: Publication
Status: Published
Schools: Chemistry
Publisher: Beilstein-Institut
ISSN: 1860-5397
Funders: National Science Foundation (CHE- 1759798) and the Royal Society (IE160304).
Date of First Compliant Deposit: 30 July 2018
Date of Acceptance: 11 July 2018
Last Modified: 30 Jul 2018 15:25
URI: http://orca-mwe.cf.ac.uk/id/eprint/113746

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