Synthesis of Aliphatic Sulfur Pentafluorides by Oxidation of SF_5-Containing Anisole, Phenols, and Anilines

摘要

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 SF_5-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-SF_5-containing maleic and succinic acids. The methods presented are the first examples of the practical synthesis of aliphatic SF_5-containing compounds from readily available aromatic ones.