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Synthesis of Aliphatic Sulfur Pentafluorides by Oxidation of SF5-Containing Anisole, Phenols, and Anilines

  1. 1.
    SYSNO ASEP0433492
    Document TypeJ - Journal Article
    R&D Document TypeJournal Article
    Subsidiary JČlánek ve WOS
    TitleSynthesis of Aliphatic Sulfur Pentafluorides by Oxidation of SF5-Containing Anisole, Phenols, and Anilines
    Author(s) Vida, Norbert (UOCHB-X) RID
    Pastýříková, Tereza (UOCHB-X) RID
    Klepetářová, Blanka (UOCHB-X) RID, ORCID
    Beier, Petr (UOCHB-X) RID, ORCID
    Number of authors4
    Source TitleJournal of Organic Chemistry. - : American Chemical Society - ISSN 0022-3263
    Roč. 79, č. 18 (2014), s. 8906-8911
    Number of pages6 s.
    Languageeng - English
    CountryUS - United States
    KeywordsSF5 ; pentafluorosulfanyl
    Subject RIVCC - Organic Chemistry
    R&D ProjectsGAP207/12/0072 GA ČR - Czech Science Foundation (CSF)
    Institutional supportUOCHB-X - RVO:61388963
    UT WOS000342121100047
    EID SCOPUS84911918059
    DOI https://doi.org/10.1021/jo501562z
    Annotation4-(Pentafluorosulfanyl)catechol, 2-amino-4-(pentafluorosulfanyl)phenol, and 2-amino-5-(pentafluorosulfanyl)phenol undergo oxidation by lead tetraacetate at ambient temperature leading to dearomatization and the formation of SF5-substituted nitrites and esters of cis,cis-hexa-2,4-dienedioic (muconic) acid in good yields. 4-(Pentafluorosulfanyl)phenol and 4-(pentafluorosulfanyl)anisole are oxidized by 3096 aqueous hydrogen peroxide in concentrated sulfuric acid to provide 2-(5-oxo-3-(pentafluorosulfanyl)-2,5-dihydrofuran-2-yl)acetic acid [3-(pentafluorosulfanyl)muconolactone] and small amounts of side products-SF5-containing maleic and succinic acids. The methods presented are the first examples of the practical synthesis of aliphatic SF5-containing compounds from readily available aromatic ones.
    WorkplaceInstitute of Organic Chemistry and Biochemistry
    Contactasep@uochb.cas.cz ; Kateřina Šperková, Tel.: 232 002 584 ; Jana Procházková, Tel.: 220 183 418
    Year of Publishing2015
Number of the records: 1  

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