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Expedient, metal-, extraction- and generally purification-free, temperature- and solvent-directed oxidation of diaryl sulfides using t-BuOCl
ID Zupanc, Anže (Author), ID Podlipnik, Črtomir (Author), ID Cerc Korošec, Romana (Author), ID Jereb, Marjan (Author)

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Abstract
An environmentally friendly, operationally simple and convenient, scalable, temperature- and solvent-directed oxidation of hydrophobic sulfides that yields sulfoxides and sulfones is presented. The conversion proceeds rapidly in a variety of green solvents, e.g., methanol, water, acetone, and acetic acid using tert-butyl hypochlorite (t-BuOCl), an easy-to-prepare and inexpensive oxidant with numerous applications in green chemistry and industry. Oxidation proceeds efficiently for challenging and poorly soluble perfluoroalkyl, heterocyclic, or polyaryl systems with multiple strongly electron-withdrawing groups, e.g. nitro, acyl, and chloro, and selectively for electron-rich systems with benzylic and enolizable competing reaction sites or multiple sulfur atoms. Various industrially important products such as pesticides, anti-HIV agents, polymer monomers and additives can be generally isolated in pure form by simply removing the reaction solvent and benign volatiles. The mechanism was explored by NMR experiments and DFT calculations. Selective oxidation of polyphenylene sulfide allowed us to synthesize more durable polymer powders and to modify the surface of the film. The depth of the oxidized layer was tuned by duration of exposure to the oxidant. The developed clean, rapid, preparative, and scalable transformation of sulfides generally without required purification can likely be extended to other similar substrates and might be of interest for synthetic and sustainability-oriented chemical processes.

Language:English
Keywords:green chemistry, oxidation, sulfones, sulfoxides, sulfides, t-BuOCl, clean synthesis
Work type:Article
Typology:1.01 - Original Scientific Article
Organization:FKKT - Faculty of Chemistry and Chemical Technology
Publication status:Published
Publication version:Version of Record
Year:2025
Number of pages:12 str.
Numbering:Vol. 486, art. 144230
PID:20.500.12556/RUL-166008 This link opens in a new window
UDC:547.279:542.943
ISSN on article:0959-6526
DOI:10.1016/j.jclepro.2024.144230 This link opens in a new window
COBISS.SI-ID:217275395 This link opens in a new window
Publication date in RUL:17.12.2024
Views:190
Downloads:65
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Record is a part of a journal

Title:Journal of cleaner production
Shortened title:J. clean. prod.
Publisher:Elsevier
ISSN:0959-6526
COBISS.SI-ID:15470597 This link opens in a new window

Licences

License:CC BY-NC 4.0, Creative Commons Attribution-NonCommercial 4.0 International
Link:http://creativecommons.org/licenses/by-nc/4.0/
Description:A creative commons license that bans commercial use, but the users don’t have to license their derivative works on the same terms.

Secondary language

Language:Slovenian
Keywords:zelena kemija, oksidacija, sulfoni, sulfoksidi, sulfidi

Projects

Funder:ARRS - Slovenian Research Agency
Project number:P1-0230
Name:Organska kemija: sinteza, struktura in aplikacija

Funder:ARRS - Slovenian Research Agency
Project number:P1-0201
Name:Fizikalna kemija

Funder:ARRS - Slovenian Research Agency
Project number:P1-0134
Name:Kemija za trajnostni razvoj

Funder:ARRS - Slovenian Research Agency
Funding programme:Young researchers

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