Tetrabutylammonium Chlorite as an Efficient Oxidant for Controlled Oxidation of Sulfides to Sulfoxides

Itabashi, Yuki; Ogata, Shuto; Shimada, Yusuke et al.

Chemistry - A European Journal, 2025, e202404279

Number of Access:745（2025-08-16 00:38 Counts）

Identifier to cite or link to this item: https://hdl.handle.net/11094/100539

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Title
Tetrabutylammonium Chlorite as an Efficient Oxidant for Controlled Oxidation of Sulfides to Sulfoxides
Creator
NRID
1000060971538 1000060971538
ORCID
0000-0002-5418-156X 0000-0002-5418-156X
researchmap permalink
yukiitabashi yukiitabashi
CreatorName
Itabashi, Yuki
CreatorName
Ogata, Shuto
CreatorName
Shimada, Yusuke
CreatorName
Kondo, Minato
NRID
1000030237763 1000030237763
CreatorName
Nishiwaki, Nagatoshi
NRID
1000020263204 1000020263204
researchmap permalink
read0185256 read0185256
Scopus Author ID
7501390753 7501390753
CreatorName
Inoue, Tsuyoshi
NRID
1000020632318 1000020632318
ORCID
0000-0002-1808-7373 0000-0002-1808-7373
researchmap permalink
pikurin3 pikurin3
Scopus Author ID
8856988200 8856988200
CreatorName
Asahara, Haruyasu
NRID
1000000379140 1000000379140
ORCID
0000-0001-8328-9249 0000-0001-8328-9249
researchmap permalink
Kei_Ohkubo Kei_Ohkubo
Scopus Author ID
7101788990 7101788990
CreatorName
Ohkubo, Kei
Subject
Chlorine dioxide
Oxygenation
Quaternary ammonium cation
Radical
Surface hydrophilization
Description
Itabashi Y., Ogata S., Shimada Y., et al. Tetrabutylammonium Chlorite as an Efficient Oxidant for Controlled Oxidation of Sulfides to Sulfoxides. Chemistry - A European Journal, (2025); https://doi.org/10.1002/chem.202404279.
Abstract
Considering the demand for organosulfur materials and the challenges associated with currently used oxidation processes, in this study, we evaluated the counter-cation of sodium chlorite (Na+ClO2−) with tetrabutylammonium chloride (Bu4N+Cl−) to synthesise tetrabutylammonium chlorite (Bu4N+ClO2−). Bu4N+ClO2− exhibited good solubility in organic solvents like chloroform (5.2 mol L−1) and ethyl acetate (2.8 mol L−1). The oxygenation reaction of organosulfides with Bu4N+ClO2− was examined in an HCl-acidic ethyl acetate solution under ambient conditions, selectively forming the corresponding sulfoxides as mono-oxygenated products. The reaction was initiated by the formation of chlorine dioxide (ClO2⋅) as an oxidant and an active species generated from Bu4N+ClO2− with HCl. This oxygenation method also enables the surface oxidation of sulfide polymers like polyphenylene sulfide (PPS) resins to increase their surface hydrophilicity. Therefore, the use of Bu4N+ClO2− for applications in organic solvents is an efficient, and highly selective approach for selective oxidation.
Publisher
John Wiley and Sons Inc
Source Title
Chemistry - A European Journal
Page
e202404279
Date of Issued
2025-02-18
Language
English
Handle URL
https://hdl.handle.net/11094/100539
PISSN
09476539
eISSN
15213765
Relation.isIdenticalTo
DOI (Publisher Version)
https://doi.org/10.1002/chem.202404279
Access Rights
open access
CopyRight
This article is licensed under a Creative Commons Attribution 4.0 International License.
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Category
学術雑誌論文 Journal Article