0433492 - ÚOCHB 2015 RIV US eng J - Článek v odborném periodiku
Vida, Norbert - Pastýříková, Tereza - Klepetářová, Blanka - Beier, Petr
Synthesis of Aliphatic Sulfur Pentafluorides by Oxidation of SF5-Containing Anisole, Phenols, and Anilines.
Journal of Organic Chemistry. Roč. 79, č. 18 (2014), s. 8906-8911. ISSN 0022-3263. E-ISSN 1520-6904
Grant CEP: GA ČR GAP207/12/0072
Institucionální podpora: RVO:61388963
Klíčová slova: SF5 * pentafluorosulfanyl
Kód oboru RIV: CC - Organická chemie
Impakt faktor: 4.721, rok: 2014 ; AIS: 1.035, rok: 2014
DOI: https://doi.org/10.1021/jo501562z

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.
Trvalý link: http://hdl.handle.net/11104/0237722