Trifluoromethanesulfonate, trifluoromethylsulfonylimide, and bis(trifluoromethylsulfonyl)imide salts and ionic liquids were synthesized from 2, 3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine (1,8-diazabicyclo[5.4.0]undec-7-ene) and 2, 3,4,6,7,8-hexahydropyrrolo[1,2-a]pyrimidine (1,5-diazabicyclo[4.3.0]non-5-ene). Their physicochemical properties, spectral parameters, and some chemical transformations were studied. I, II, X = H: Y = F 3 CSO 2 O (a), F 3 CSO 2 NH (b), (F 3 CSO 2 ) 2 N (c); X = Pr: Y = Cl (d), (F 3 CSO 2 ) 2 N (e); X = Ph, Y = (F 3 CSO 2 ) 2 N (f); X = F 3 CSO 2 , Y = F 3 CSO 2 O (g).First ionic liquids based on 1,8-diazabicyclo[5.4.0]-undec-7-ene (DBU,2,3,4,6,7,8,9,azepine) cations and various anions (Cl, Br, OTs, OTf) were reported previously [1-3]. Of particular interest are ionic liquids containing bis(trifluoromethylsulfonyl)imide anion (CF 3 SO 2 ) 2 N -which considerably reduces the melting point and viscosity of ionic liquids, as compared to other anions. In addition, organic salts with trifluoromethylsulfonylimide and other perfluoroalkylsulfonylimide anions are mainly hydrophobic and are characterized by high thermal and electrochemical stability [4][5][6]. First ionic liquids with trifluoromethylsulfonylimide anion were synthesized on the basis of imidazolium cation in 1995-96 [7, 8], and they subsequently found wide application [9][10][11].In the present communication we describe the synthesis of new salts and ionic liquids derived from DBU (I) and 1,5-diazabicyclo[4.3.0]non-5-ene (II, DBN, 2,3,4,6,7,8-hexahydropyrrolo[1,2-a]pyrimidine) and containing trifluoromethanesulfonate, trifluoromethylsulfonylimide, and bis(trifluoromethylsulfonyl)imide anions. The initial nitrogen-containing bases, DBU and DBN, are readily obtained from ε-caprolactam and pyrrolidin-2-one, respectively, and their synthetic and commercial accessibilities are quite comparable with those of 1-alkylimidazoles that are starting compounds for the preparation of most known ionic liquids.Almost similar structures of DBU (I) and DBN (II) in salts (X = N) and ionic liquids (X = R) makes it possible to use spectral parameters of readily obtainable and identifiable salts DBUH + Y -and DBNH + Yfor identification of ionic liquids DBUR + Y -and DBNR + Y -which are synthesized by different methods.Trifluoromethanesulfonate, trifluoromethylsulfonylimide, and bis(trifluoromethylsulfonyl)imide DBU and DBN salts Ia-Ic and IIa-IIc were prepared in quantitative yield by mixing equimolar amounts of the corresponding base and trifluoromethanesulfonic acid CF 3 SO 3 H, trifluoromethanesulfonamide CF 3 S O 2 NH 2 , o r t r i f luo r o me t h a n s u l f o n i mi d e (CF 3 SO 2 ) 2 NH under solvent-free conditions or in chloroform at room temperature. The products were analyzed after removal of the solvent without additional purification. The isolated salts were colorless
