Preparation of the first ortho-substituted pentafluorosulfanylbenzenes

The preparation of the first ortho-substituted pentafluorosulfanylbenzenes was achieved. Oxidative fluorination (AgF2) of a series of aromatic disulfides containing different substituents ortho to the disulfide moiety gave only one ortho-substituted SF5-benzene, namely 1-fluoro-4-nitro-2-pentafluorosulfanylbenzene. This compound has been transformed into a variety of other ortho-substituted SF5-benzenes by nucleophilic substitution reactions.