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Synthesis of Aliphatic Sulfur Pentafluorides by Oxidation of SF5-Containing Anisole, Phenols, and Anilines
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SYSNO ASEP 0433492 Document Type J - Journal Article R&D Document Type Journal Article Subsidiary J Článek ve WOS Title Synthesis 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, ORCIDNumber of authors 4 Source Title Journal of Organic Chemistry. - : American Chemical Society - ISSN 0022-3263
Roč. 79, č. 18 (2014), s. 8906-8911Number of pages 6 s. Language eng - English Country US - United States Keywords SF5 ; pentafluorosulfanyl Subject RIV CC - Organic Chemistry R&D Projects GAP207/12/0072 GA ČR - Czech Science Foundation (CSF) Institutional support UOCHB-X - RVO:61388963 UT WOS 000342121100047 EID SCOPUS 84911918059 DOI https://doi.org/10.1021/jo501562z Annotation 4-(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. Workplace Institute of Organic Chemistry and Biochemistry Contact asep@uochb.cas.cz ; Kateřina Šperková, Tel.: 232 002 584 ; Jana Procházková, Tel.: 220 183 418 Year of Publishing 2015
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