title: Synthesis of aliphatic sulfur pentafluorides by oxidation of SF₅-containing anisole, phenols, and anilines.
abstract: 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 nitriles and esters of cis,cis-hexa-2,4-dienedioic (muconic) acid in good yields. 4-(Pentafluorosulfanyl)phenol and 4-(pentafluorosulfanyl)anisole are oxidized by 30% 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.
authors.affiliation: Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic , Flemingovo nám. 2, 166 10 Prague 6, Czech Republic.
authors.forename: Norbert
authors.initials: N
authors.lastname: Vida
authors.forename: Tereza
authors.initials: T
authors.lastname: Pastýříková
authors.forename: Blanka
authors.initials: B
authors.lastname: Klepetářová
authors.forename: Petr
authors.initials: P
authors.lastname: Beier
mesh_terms: D000814:Aniline Compounds / Q000737:chemistry*; D000840:Anisoles / Q000737:chemistry*; D002396:Catechols / Q000737:chemistry*; D005459:Fluorides / Q000138:chemical synthesis* / Q000737:chemistry*; D005663:Furans / Q000138:chemical synthesis* / Q000737:chemistry; D006861:Hydrogen Peroxide / Q000737:chemistry*; D007783:Lactones / Q000138:chemical synthesis* / Q000737:chemistry; D010084:Oxidation-Reduction; D010636:Phenols / Q000737:chemistry*; D013457:Sulfur Compounds / Q000138:chemical synthesis* / Q000737:chemistry*
chemical_list: C000595494:2-(5-oxo-3-(pentafluorosulfanyl)-2,5-dihydrofuran-2-yl)acetic acid(3-(pentafluorosulfanyl)muconolactone); C000595493:2-amino-5-(pentafluorosulfanyl)phenol; C000595491:4-(pentafluorosulfanyl)catechol; D000814:Aniline Compounds; D000840:Anisoles; D002396:Catechols; D005663:Furans; D007783:Lactones; D010636:Phenols; D013457:Sulfur Compounds; C523090:sulfur fluoride; D006861:Hydrogen Peroxide; D005459:Fluorides