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

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 uni...

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Autores principales: Mironova, Irina A, Postnikov, Pavel S, Yusubova, Rosa Y, Yoshimura, Akira, Wirth, Thomas, Zhdankin, Viktor V, Nemykin, Victor N, Yusubov, Mekhman S
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2018
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6071709/
https://www.ncbi.nlm.nih.gov/pubmed/30112090
http://dx.doi.org/10.3762/bjoc.14.159
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author Mironova, Irina A
Postnikov, Pavel S
Yusubova, Rosa Y
Yoshimura, Akira
Wirth, Thomas
Zhdankin, Viktor V
Nemykin, Victor N
Yusubov, Mekhman S
author_facet Mironova, Irina A
Postnikov, Pavel S
Yusubova, Rosa Y
Yoshimura, Akira
Wirth, Thomas
Zhdankin, Viktor V
Nemykin, Victor N
Yusubov, Mekhman S
author_sort Mironova, Irina A
collection PubMed
description 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.
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spelling pubmed-60717092018-08-15 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 Yusubov, Mekhman S Beilstein J Org Chem Full Research Paper 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. Beilstein-Institut 2018-07-20 /pmc/articles/PMC6071709/ /pubmed/30112090 http://dx.doi.org/10.3762/bjoc.14.159 Text en Copyright © 2018, Mironova et al. https://creativecommons.org/licenses/by/4.0https://www.beilstein-journals.org/bjoc/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/4.0). Please note that the reuse, redistribution and reproduction in particular requires that the authors and source are credited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms)
spellingShingle Full Research Paper
Mironova, Irina A
Postnikov, Pavel S
Yusubova, Rosa Y
Yoshimura, Akira
Wirth, Thomas
Zhdankin, Viktor V
Nemykin, Victor N
Yusubov, Mekhman S
Preparation and X-ray structure of 2-iodoxybenzenesulfonic acid (IBS) – a powerful hypervalent iodine(V) oxidant
title Preparation and X-ray structure of 2-iodoxybenzenesulfonic acid (IBS) – a powerful hypervalent iodine(V) oxidant
title_full Preparation and X-ray structure of 2-iodoxybenzenesulfonic acid (IBS) – a powerful hypervalent iodine(V) oxidant
title_fullStr Preparation and X-ray structure of 2-iodoxybenzenesulfonic acid (IBS) – a powerful hypervalent iodine(V) oxidant
title_full_unstemmed Preparation and X-ray structure of 2-iodoxybenzenesulfonic acid (IBS) – a powerful hypervalent iodine(V) oxidant
title_short Preparation and X-ray structure of 2-iodoxybenzenesulfonic acid (IBS) – a powerful hypervalent iodine(V) oxidant
title_sort preparation and x-ray structure of 2-iodoxybenzenesulfonic acid (ibs) – a powerful hypervalent iodine(v) oxidant
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6071709/
https://www.ncbi.nlm.nih.gov/pubmed/30112090
http://dx.doi.org/10.3762/bjoc.14.159
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