The Study On The Synthesis And Applications Of Functional Ionic Liquids

As newly-developed green media, ionic liquids can be used to subsitute the traditional solvents to overcome the drawbacks of the latter such as volatility, toxicity, flammability, and difficulties to store or recycle.The transformation of alcohols to aldehydes is a key reaction in synthetic organic chemistry. We have found that [Bmim][Br₃] can be used as an oxidising agent to convert alcohols to aldehydes and ketones in mild conditions and good yields, and the use of it both as oxidising and brominating reagent in the one-pot synthesis of β-bromoethyl esters from benzyl alcohols and diols has also been studied.In view of the emerging importance of ILs as reaction media in organic synthesis, several groups have recently focused on the synthesis of chiral ionic liquids (CILs) for their potential particular applications to chiral discrimination, including asymmetric synthesis and optical resolution of racemates. Here we reporte that two kinds of novel chiral ionic liquids based on imidazolium have been synthesized from chiral pool by a simple and straightforward procedure in good overall yields (44-60%). The application of ionic liquid l-butyl-3-methylimidazolium bromide as excellent "green" reactant and solvent in nucleophilic substitution step of this procedure has also been studied. As the subsequent study, we decided to use the CILs we synthesized, as the phase transfer catalyst (PTC), in the asymmetric synthesis of α-aminoacid.This dissertation mainly falls into two parts: the literature review and the experiment results discussion. In the review section, we mainly introduced the development, buildup, synthesis and application of ILs, especially the functional ILs. While in the experiment section, we described three parts: (1) synthesis of new chiral ionic liquids from natural acids and their applications in enantioselective Michael addition. (2) an alternative oxidising and brominating method converting alcohols to aldehydes and β-bromoethyl esters using ionic liquid [Bmim][Br₃]. (3) Catalytic asymmetric phase-transfer reaction using tartrate-derived and some other asymmetric organocatalysts.