Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic , Flemingovo nám. 2, 166 10 Prague 6, Czech Republic.
J Org Chem. 2014 Sep 19;79(18):8906-11. doi: 10.1021/jo501562z. Epub 2014 Aug 27.
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.
4-（五氟硫基）邻苯二酚、2-氨基-4-（五氟硫基）苯酚和 2-氨基-5-（五氟硫基）苯酚在环境温度下被四乙酸铅氧化，导致去芳构化，并以良好的收率生成 SF5 取代的腈和顺式，顺式-己-2,4-二烯二（富马酸）酸的酯。4-（五氟硫基）苯酚和 4-（五氟硫基）苯甲醚在浓硫酸中用 30%过氧化氢氧化，得到 2-（5-氧代-3-（五氟硫基）-2,5-二氢呋喃-2-基）乙酸[3-（五氟硫基）富马酸内酯]和少量副产物-SF5 含有的马来酸和琥珀酸。所提出的方法是首次从易得的芳族化合物实际合成脂肪族 SF5 化合物的实例。
