Reactions of the Perfluoroalkyltriazapentadiene Ph2N3C2(C3F7)2H with Acids, Bases, and Water

Treatment of the bis(perfluoroalkyl)triazapentadiene PhN=C(C3F7)—N=C(C3F7)—NHPh, 2, with bases affords salts of the conjugate base. Alkylation of the Na+ salt with Ch3l yields PhN==C(C3F7)-N=C(C3F7)~NMePh. The crystal structure of [Bu4N][Ph2N3C2(C3F7)2] demonstrates a twisted, zigzag geometry for the anion in the solid state, but in solution, it is conformationally unstable. Both compounds are stable in aqueous methanol, but hydrolysis occurs under acidic conditions. Protonation with CF3S03H acid occurs at the sp^2 nitrogen to give [PhN-h-HC3F7)—N—C(C3F7)— NHPh][CF3SO3]. Heating 2 in CF3S03H produces 2,4-bis(heptafluoropropyl)-1,3-quinazoline.