Synthesis Of Imidazolium Ionic Liquid Containing Perfluoropolyether Chain And Research Of Fluorous Chiral Auxiliary Sulfinamide

The rapid development of fluorine chemistry is because of the unique physical, chemical properties and physiological activity of the organic products in which hydrogen was replaced by fluorine. Thus, the synthesis and application of fluorinated compounds were studied in many fields including many important technology and industrial projects, pharmaceuticals, pesticides, industrial catalysis and so on. In this dissertation, the synthesis of imidazolium ionic liquid containing perfluoropolyether chain and fluorous chiral auxiliary sulfinamide were researched. The mainly work includes two chapters as follow:Part 1:In recent years, as a class of novel environmental benign solvents, ionic liquids have been applied in organic synthesis and polymer materials because of their fascinating properties than many of the traditional solvents. In this paper, we reported the synthesis of imidazolium salts containing perfluoropolyether chain in high yields. The surface tensions of these imidazolium salts have been investigated. A series of parameters, including critical micelle concentration (cmc) and surface tension at the cmc (γcmc), indicated that they have good surface activity and could reduce the surface tension of water significantly.Part 2:As a widely used chiral auxiliary agent, chiral tert-butylsulfinamide has become an important target molecule in organic synthesis because of its high asymmetric induction and the readily removability of tert-butylsulfinyl after reaction. Therefore, perfluorinated iodide 8 was transfered into the corresponding Grignard reagent, and then reacted with carbonyl compounds to afford alcohols 9 containing one to three perfluoropolyether chain chains. Alcohols 9 were then transfered into the corresponding Grignard reagent after the hydroxyl was substituted by halogenated reagents, and then the corresponding Grignard reagent react with SO2 and SOC12 to give the Sulfinyl Chloride 11. Unfortunately, we failed to get the desired product when racemic Sulfinyl Chloride 11 was transfered to Chiral Sulfinamide by dynamic resolution after different conditions have been tried. It is probably due to the weak stability of compound 11, and it is easy to hydrolyze.