Asian Research Thesis Index

Abstract

This dissertation describes the designing, synthesis and applications of a novel functional ionic liquid named as DMF-like Multipurpose Functional Ionic Liquid (MFIL). Its designing is based on attaching N-methylformamide functionality to imidazolium ring through two carbon spacings. It has been synthesized through a viable synthetic scheme in quantitative amount and characterized through latest spectroscopic techniques. After this, its physical parameters like melting point, viscosity, thermal stability, and miscibility behavior were determined. The values of all physical parameters were quite appropriate for it to behave like reasonable ionic liquid to act as solvent or solvent-cum-reagent. With all its structural and physical profile completed, it was evaluated for its efficiency to prove as a better substitute of ordinary DMF. It is fact that DMF does not merely act as a solvent for dissolving reactants, instead it can act as an active reaction media that affects the outcome of certain reactions. In addition to this, it is also used as activator of certain inorganic and organometallic reagents and as precursor for the synthesis of highly valuable Vilsmier reagent. The novel DMF-like multipurpose functional ionic liquid has been evaluated as a better substitute for some of ordinary DMF-dependent reactions like nucleophillic substitution reaction, and as an activator of sodium periodate. Apart from this, the ionic liquid version of Vilsmier reagent was prepared from DMF-like ionic liquid and it was proved to be more stable, water resistant and efficient substitute of ordinary Vilsmier reagent. It was evaluated for some Vilsmier reagent promoted reactions like direct chlorination and iodination of alcohols, N-alkylation of phthalimides, Beckmann rearrangement, and Lossen rearrangement. More interestingly same reagent was also found to be better alternative to Mitsunobu reagent and some of the Mitsunobu reagent catalyzed reactions have been executed successfully. The ionic liquid-based Vilsmier reagent was also used a dehydrating reagent for some reaction occurring by dehydration. Further investigation into the applications and scope of ionic liquid-based Vilsmier reagent indicated that variety of Pummerer rearrangements can be accomplished through it with possibly best yields. All of the above reactions were found to produce relatively more efficient results in DMF-like ionic liquid as compared to ordinary DMF in terms of better yields and faster reaction rates. Apart from this, green reaction conditions, softer reaction condition, easy recovery of products and recycling of ionic reagents thus minimizing the generation of chemical waste were the major salient aspects of the current methodology. Therefore, ionic liquid version of DMF was proved to be efficient substitute of an ordinary DMF. The novel DMF-like MFIL has been designed, synthesized and checked for its potential to accomplish wide range of useful chemical transformations. This has become first of the functional ionic liquids that can perform more the one task. This is in contrast to other functional ionic liquids which are designed as task specific in their performance i.e. they can perform only one specific task. Due to unparallel ability DMF-like functional ionic liquid to promote multifarious applications, it was found to be “multipurpose” functional ionic liquid therefore it has been named as DMF-like multipurpose functional ionic liquid. This is going to be the first example of this kind of ionic liquids thus justifying the title of the thesis.

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