Synthesis and nucleophilic aromatic substitution of 3-fluoro-5-nitro-1-(pentafluorosulfanyl)benzene

Abstrakt

3-Fluoro-5-nitro-1-(pentafluorosulfanyl) benzene was prepared by three different ways: as a byproduct of direct fluorination of 1,2-bis-(3-nitrophenyl) disulfane, by direct fluorination of 4-nitro-1-(pentafluorosulfanyl) benzene, and by fluorodenitration of 3,5-dinitro-1-(pentafluorosulfanyl) benzene. The title compound was subjected to a nucleophilic aromatic substitution of the fluorine atom with oxygen, sulfur and nitrogen nucleophiles affording novel (pentafluorosulfanyl) benzenes with 3,5-disubstitution pattern.

Vicarious nucleophilic substitution of the title compound with carbon, oxygen, and nitrogen nucleophiles provided 3-fluoro-5-nitro-1-(pentafluorosulfanyl) benzenes substituted in position four.

Klíčová slova

• direct fluorination
• fluorine
• nucleophilic aromatic substitution
• pentafluorosulfanyl group
• vicarious nucleophilic substitution