Date of Award

Fall 2005

Document Type

Dissertation

Degree Name

Doctor of Philosophy in Chemistry - (Ph.D.)

Department

Chemistry and Environmental Science

First Advisor

Sanjay V. Malhotra

Second Advisor

Edgardo Tabion Farinas

Third Advisor

Tamara M. Gund

Fourth Advisor

Zafar Iqbal

Fifth Advisor

Sharon Lall-Ramnarine

Abstract

Recently, ionic liquids have attracted a lot of attention as novel materials for organic transformations. This is due to their unique properties, which make them suitable substitutes for organic solvents. Most of the available literature is focused on the application of imidazolium-based ionic liquids for organic reactions, while very limited information is available on the application of pyridinium-based ionic liquids.

In this study, two different ionic liquids, 1 -ethyl-pyridinium tetrafluoroborate ([EtPy]+[BF4]-) and 1 -ethyl-pyridinium trifluoroacetate ([EtPy]+[CF3COO]-) have been investigated. Compared to previous reports, the synthetic technique for preparation of Nethyl-pyridinium-based ionic liquids has been improved. Systematic studies of five reactions in both these ionic liquids have yielded a greater understanding. These reactions include (i) Diels-Alder reaction; (ii) Friedel-Crafts alkylation; (iii) FriedelCrafts acylation; (iv) asymmetric Friedel-Crafis reaction; and (v) asymmetric reduction of ketones. Moreover, the effects of various catalysts, solvents and temperatures have been studied. Also, the reusability of ionic liquids for these reactions has been tested and the optimal reaction conditions have been determined. These studies have led to the development of new methodologies for all of these reactions in both these N-ethylpyridinium-based ionic liquids.

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