Reactions of 1,3,5-tris(fluorosulfonyl)benzene with some nucleophilic reagents

The reactions of 1,3,5-tris(fluorosulfonyl)benzene 1 with nucleophilic agents were investigated. It was found that morpholine, β,β,β-trifluoroethanol in the presence of triethylamine and sodium azide formed corresponding 1,3,5-trisulfonyl derivatives. In contrast, nucleophiles such as aniline, thiourea, and potassium thiocyanate do not react with compound 1 even in excess and under moderate heating. The conditions for the selective fluorine atom substitution in one SO2F group with morpholine, DMAP and aniline in the presence of triethylamine as well as in two SO2F groups with DMAP were found. Anionic σ-complex of compound 1 with nitromethane was isolated as individual compound.