{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,12]],"date-time":"2026-10-12T20:43:00Z","timestamp":1791837780917,"version":"4.3.4"},"reference-count":28,"publisher":"Wiley","issue":"17","license":[{"start":{"date-parts":[[2025,2,18]],"date-time":"2025-02-18T00:00:00Z","timestamp":1739836800000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"DOI":"10.13039\/501100001691","name":"Japan Society for the Promotion of Science","doi-asserted-by":"publisher","award":["JP23K13709"],"award-info":[{"award-number":["JP23K13709"]}],"id":[{"id":"10.13039\/501100001691","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100001691","name":"Japan Society for the Promotion of Science","doi-asserted-by":"publisher","award":["JP23K18542"],"award-info":[{"award-number":["JP23K18542"]}],"id":[{"id":"10.13039\/501100001691","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100001691","name":"Japan Society for the Promotion of Science","doi-asserted-by":"publisher","award":["JP24K21770"],"award-info":[{"award-number":["JP24K21770"]}],"id":[{"id":"10.13039\/501100001691","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100001863","name":"New Energy and Industrial Technology Development Organization","doi-asserted-by":"publisher","award":["Grant 17101509-0"],"award-info":[{"award-number":["Grant 17101509-0"]}],"id":[{"id":"10.13039\/501100001863","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":["chemistry-europe.onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["Chemistry A European J"],"published-print":{"date-parts":[[2025,3,20]]},"abstract":"<jats:title>Abstract<\/jats:title><jats:p>Considering the demand for organosulfur materials and the challenges associated with currently used oxidation processes, in this study, we evaluated the counter\u2010cation of sodium chlorite (Na<jats:sup>+<\/jats:sup>ClO<jats:sub>2<\/jats:sub><jats:sup>\u2212<\/jats:sup>) with tetrabutylammonium chloride (Bu<jats:sub>4<\/jats:sub>N<jats:sup>+<\/jats:sup>Cl<jats:sup>\u2212<\/jats:sup>) to synthesise tetrabutylammonium chlorite (Bu<jats:sub>4<\/jats:sub>N<jats:sup>+<\/jats:sup>ClO<jats:sub>2<\/jats:sub><jats:sup>\u2212<\/jats:sup>). Bu<jats:sub>4<\/jats:sub>N<jats:sup>+<\/jats:sup>ClO<jats:sub>2<\/jats:sub><jats:sup>\u2212<\/jats:sup> exhibited good solubility in organic solvents like chloroform (5.2\u2005mol\u2009L<jats:sup>\u22121<\/jats:sup>) and ethyl acetate (2.8\u2005mol\u2009L<jats:sup>\u22121<\/jats:sup>). The oxygenation reaction of organosulfides with Bu<jats:sub>4<\/jats:sub>N<jats:sup>+<\/jats:sup>ClO<jats:sub>2<\/jats:sub><jats:sup>\u2212<\/jats:sup> was examined in an HCl\u2010acidic ethyl acetate solution under ambient conditions, selectively forming the corresponding sulfoxides as mono\u2010oxygenated products. The reaction was initiated by the formation of chlorine dioxide (ClO<jats:sub>2<\/jats:sub>\u22c5) as an oxidant and an active species generated from Bu<jats:sub>4<\/jats:sub>N<jats:sup>+<\/jats:sup>ClO<jats:sub>2<\/jats:sub><jats:sup>\u2212<\/jats:sup> 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 Bu<jats:sub>4<\/jats:sub>N<jats:sup>+<\/jats:sup>ClO<jats:sub>2<\/jats:sub><jats:sup>\u2212<\/jats:sup> for applications in organic solvents is an efficient, and highly selective approach for selective oxidation.<\/jats:p>","DOI":"10.1002\/chem.202404279","type":"journal-article","created":{"date-parts":[[2025,1,7]],"date-time":"2025-01-07T03:49:56Z","timestamp":1736221796000},"update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":4,"title":["Tetrabutylammonium Chlorite as an Efficient Oxidant for Controlled Oxidation of Sulfides to Sulfoxides"],"prefix":"10.1002","volume":"31","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-5418-156X","authenticated-orcid":false,"given":"Yuki","family":"Itabashi","sequence":"first","affiliation":[{"name":"Institute for Open and Transdisciplinary Research Initiatives (OTRI) Osaka University  1\u20136 Yamada-oka, Suita Osaka 565\u20130871 Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Shuto","family":"Ogata","sequence":"additional","affiliation":[{"name":"Graduate School of Pharmaceutical Sciences Osaka University  1\u20136 Yamada-oka, Suita Osaka 565\u20130871 Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Yusuke","family":"Shimada","sequence":"additional","affiliation":[{"name":"Graduate School of Pharmaceutical Sciences Osaka University  1\u20136 Yamada-oka, Suita Osaka 565\u20130871 Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Minato","family":"Kondo","sequence":"additional","affiliation":[{"name":"School of Engineering Science Kochi University of Technology  Tosayamada, Kami, Kochi 782\u20138502 Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-6052-8697","authenticated-orcid":false,"given":"Nagatoshi","family":"Nishiwaki","sequence":"additional","affiliation":[{"name":"School of Engineering Science Kochi University of Technology  Tosayamada, Kami, Kochi 782\u20138502 Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Tsuyoshi","family":"Inoue","sequence":"additional","affiliation":[{"name":"Institute for Open and Transdisciplinary Research Initiatives (OTRI) Osaka University  1\u20136 Yamada-oka, Suita Osaka 565\u20130871 Japan"},{"name":"Graduate School of Pharmaceutical Sciences Osaka University  1\u20136 Yamada-oka, Suita Osaka 565\u20130871 Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-1808-7373","authenticated-orcid":false,"given":"Haruyasu","family":"Asahara","sequence":"additional","affiliation":[{"name":"Institute for Open and Transdisciplinary Research Initiatives (OTRI) Osaka University  1\u20136 Yamada-oka, Suita Osaka 565\u20130871 Japan"},{"name":"Graduate School of Pharmaceutical Sciences Osaka University  1\u20136 Yamada-oka, Suita Osaka 565\u20130871 Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-8328-9249","authenticated-orcid":false,"given":"Kei","family":"Ohkubo","sequence":"additional","affiliation":[{"name":"Institute for Open and Transdisciplinary Research Initiatives (OTRI) Osaka University  1\u20136 Yamada-oka, Suita Osaka 565\u20130871 Japan"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2025,2,18]]},"reference":[{"key":"e_1_2_8_1_1","doi-asserted-by":"publisher","DOI":"10.1021\/cr00038a002"},{"key":"e_1_2_8_2_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.jafc.6b01564"},{"key":"e_1_2_8_3_1","doi-asserted-by":"publisher","DOI":"10.1039\/D1SC05070B"},{"key":"e_1_2_8_4_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202203908"},{"key":"e_1_2_8_5_1","doi-asserted-by":"publisher","DOI":"10.1039\/C9GC03713F"},{"key":"e_1_2_8_6_1","doi-asserted-by":"publisher","DOI":"10.1021\/ar400258p"},{"key":"e_1_2_8_7_1","doi-asserted-by":"publisher","DOI":"10.1021\/ic060730t"},{"key":"e_1_2_8_8_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.molcata.2009.03.034"},{"key":"e_1_2_8_9_1","doi-asserted-by":"publisher","DOI":"10.1039\/D0ME00032A"},{"key":"e_1_2_8_10_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.tetlet.2014.05.080"},{"key":"e_1_2_8_11_1","doi-asserted-by":"publisher","DOI":"10.1080\/00397919808004876"},{"key":"e_1_2_8_12_1","first-page":"2","volume":"1","author":"Meenakshisundaram S.","year":"1999","journal-title":"J. Chem. Res. (S)"},{"key":"e_1_2_8_13_1","doi-asserted-by":"publisher","DOI":"10.1021\/jo201972k"},{"key":"e_1_2_8_14_1","doi-asserted-by":"publisher","DOI":"10.1021\/cr300527g"},{"key":"e_1_2_8_15_1","doi-asserted-by":"crossref","unstructured":"H. Vogt J. Balej J.\u2005E. Bennett P. Wintzer S.\u2005A. Sheikh P. Gallone S. Vasudevan K. Pelin Chlorine Oxides Chlorine Oxygen Acids In Ullmann's Encyclopedia of Industrial Chemistry Wiley-VCH Weinheim Germany 2010.","DOI":"10.1002\/14356007.a06_483.pub2"},{"key":"e_1_2_8_16_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.201710945"},{"key":"e_1_2_8_17_1","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200801521"},{"key":"e_1_2_8_18_1","doi-asserted-by":"publisher","DOI":"10.1039\/D3CC01057K"},{"key":"e_1_2_8_19_1","doi-asserted-by":"publisher","DOI":"10.1002\/cjce.5450820323"},{"key":"e_1_2_8_20_1","doi-asserted-by":"publisher","DOI":"10.1002\/poc.3619"},{"key":"e_1_2_8_21_1","doi-asserted-by":"publisher","DOI":"10.1021\/jo01312a004"},{"key":"e_1_2_8_22_1","doi-asserted-by":"publisher","DOI":"10.1021\/jo01294a058"},{"key":"e_1_2_8_23_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4020(01)97963-3"},{"key":"e_1_2_8_24_1","doi-asserted-by":"publisher","DOI":"10.1039\/C9CC01037H"},{"key":"e_1_2_8_25_1","doi-asserted-by":"publisher","DOI":"10.1038\/s41428-021-00544-5"},{"key":"e_1_2_8_26_1","doi-asserted-by":"publisher","DOI":"10.1021\/jp992693f"},{"key":"e_1_2_8_27_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja035156o"},{"key":"e_1_2_8_28_1","unstructured":"DFT calculations showed that the activation energies for the reaction of ClO\u2022with diphenyl sulfide and diphenyl sulfoxide are 0.9 and 4.8\u2005kcal\u2009mol\u22121 respectively. The energies and coordinates for these calculations are provided in the SI."}],"container-title":["Chemistry \u2013 A European Journal"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/chem.202404279","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,12]],"date-time":"2025-10-12T09:08:14Z","timestamp":1760260094000},"score":1,"resource":{"primary":{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/10.1002\/chem.202404279"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2025,2,18]]},"references-count":28,"journal-issue":{"issue":"17","published-print":{"date-parts":[[2025,3,20]]}},"alternative-id":["10.1002\/chem.202404279"],"URL":"https:\/\/doi.org\/10.1002\/chem.202404279","archive":["Portico"],"relation":{},"ISSN":["0947-6539","1521-3765"],"issn-type":[{"value":"0947-6539","type":"print"},{"value":"1521-3765","type":"electronic"}],"subject":[],"published":{"date-parts":[[2025,2,18]]},"assertion":[{"value":"2024-11-20","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2025-02-18","order":3,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}],"article-number":"e202404279"}}