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

doi:10.3762/bjoc.14.159

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

Chemistry & Biochemistry

Research output: Contribution to journal › Article › peer-review

12 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 language	English (US)
Pages (from-to)	1854-1858
Number of pages	5
Journal	Beilstein Journal of Organic Chemistry
Volume	14
DOIs	https://doi.org/10.3762/bjoc.14.159
State	Published - 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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title = "Preparation and X-ray structure of 2-iodoxybenzenesulfonic acid (IBS) – A powerful hypervalent iodine(V) oxidant",

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.",

keywords = "2-iodoxybenzenesulfonic acid, Hypervalent iodine, Iodine, Oxidation, X-ray",

author = "Mironova, {Irina A.} and Postnikov, {Pavel S.} and Yusubova, {Rosa Y.} and Akira Yoshimura and Thomas Wirth and Zhdankin, {Viktor V.} and Nemykin, {Victor N.} and Yusubov, {Mekhman S.}",

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: {\textcopyright} 2018 Mironova et al.",

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AU - Mironova, Irina A.

AU - Postnikov, Pavel S.

AU - Yusubova, Rosa Y.

AU - Yoshimura, Akira

AU - Wirth, Thomas

AU - Zhdankin, Viktor V.

AU - Nemykin, Victor N.

AU - Yusubov, Mekhman S.

N1 - 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.

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N2 - 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.

AB - 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.

KW - 2-iodoxybenzenesulfonic acid

KW - Hypervalent iodine

KW - Iodine

KW - Oxidation

KW - X-ray

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

Abstract

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