Replacement of the nitro groups in 1,3,5-trinitrobenzene on treatment with polyfluorinated alcohols

Abstract

Depending on the conditions, polyfluorinated alcohols R_fCH₂OH [R_f = CF₃, H(CF₂)_n; n = 2, 4, 6, 8] replace one or two nitro groups in 1,3,5-trinitrobenzene in the presence of K₂CO₃ in N-methylpyrrolidone to give the previously unknown 1-polyfluoro-alkoxy-3,5-dinitrobenzenes or 1,3-di(polyfluoroalkoxy)-5-nitrobenzenes; the reaction is successful due to the high acidity of R_fCH₂OH (pK_a≅12).