Organic Polycationic Salts - Syntheses and Applications

Acyclic tertiary diamines and 1,4,7,10-tetraazacyclododecane with fluorine-containing β-diketones: Leading to low melting ionic adducts

“…While all of the dicationic salts are highly soluble in non-aqueous solvents, the liquid salts (3,4,10,13,14,16) are sparingly miscible with water. Aqueous solutions of the remaining salts were maintained at 25 8C for several days with no formation of suspension/precipitate.…”

“…While a very large number of quaternary tetraalkyl ammonium salts [2][3][4][5][6][7][8][9][10][11], have been synthesized since the report of a liquid ammonium salt, EtNH 3 + NO 3 À , early in the last century, there are few quaternary trialkyl ammonium (R 3 NH + ) compounds. Derivatives of some of the latter have been proposed for biological applications [12][13][14][15].…”

“…Polyammonium organic salts have been synthesized in abundance giving rise to topographical categories including dendrimeric, cyclic, pendant and cyclic species [10,11]. Physical properties of these materials with two or more charged sites distributed within the covalent structure of the cationic species vary greatly, and as is typical of such salts, the anion exerts a marked influence.…”

Perfluoro alkyl 1,3-diketonates of cyclic and acyclic secondary amines

“…Analogously, other cyclic amines (B, D, E, F) were reacted with 4 to form salts (13,16,18,20) in varying yields. Additional 1,3-diketones (1, 2, 3, 5) were also reacted under similar conditions with morpholine (A) to form ionic liquids (6,7,8,10); N-acetylmorpholine (B) with 1,3-diketones (1, 3, 5) gave ionic liquids (11,12,14); 3-methyl-N-acetyl piperidine (C) with 5 produced 15; 2,2,6,6, tetramethyl-4-aminopiperidine (D) with 3 gave 17; 4,4-dimethylimidazoline (E) with 4 formed 18; and 1,3-bispiperidine propane (F) with 1 produced 19 (Scheme 1, Table 1). …”

“…Cyclic trialkylammonium cations have been utilized in a one-pot, two step syntheses of new functionalized ionic liquids using Michael-type addition reactions [3]. While a very large number of quaternary tetraalkyl ammonium salts have been synthesized [4][5][6][7][8][9][10][11][12][13], there were few quaternary trialkyl ammonium (R 3 NH + ) compounds until the recently reported reactions of N,N,N 0 ,N 0 -tetramethylalkane diamines with fluorine-containing 1,3-diketones to form bis-quaternary ammonium salts which often are rather low melting [14].…”