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

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.