The New Jersey Institute of Technology's
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Title:	Study of organic reactions in pyridinium-based ionic liquids
Author:	Xiao, Ying
View Online:	njit-etd2006-041 (xix, 138 pages ~ 6.3 MB pdf)
Department:	Department of Chemistry and Environmental Science
Degree:	Doctor of Philosophy
Program:	Chemistry
Document Type:	Dissertation
Advisory Committee:	Malhotra, Sanjay V. (Committee chair) Farinas, Edgardo Tabion (Committee member) Gund, Tamara M. (Committee member) Iqbal, Zafar (Committee member) Lall-Ramnarine, Sharon (Committee member)
Date:	2006-01
Keywords:	Pyridinium Ionic liquid Organic reactions Asymetric reactions Friedel-Crafts reaction Diels-Alder reaction
Availability:	Unrestricted
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.