Development of a Multipolymer Reaction and Polyfunctional Polymeric Catalysts

This dissertation, "Development of a Multipolymer Reaction and Polyfunctional Polymeric Catalysts" by 鍾韻盈, Wan-ying, Cecilia, Chung, was obtained from The University of Hong Kong (Pokfulam, Hong Kong) and is being sold pursuant to Creative Commons: Attribution 3.0 Hong Kong License. The content of this dissertation has not been altered in any way. We have altered the formatting in order to facilitate the ease of printing and reading of the dissertation. All rights not granted by the above license are retained by the author. Abstract: Abstract of thesis entitled DEVELOPMENT OF A MULTIPOLYMER REACTION AND POLYFUNCTIONAL POLYMERIC CATALYSTS Submitted by Chung Wan Ying Cecilia for the Degree of Doctor of Philosophy at The University of Hong Kong in March 2008 Polymer-supported reagents and catalysts have long been used in organic synthesis because they simplify product purification and can often be recycled. Simultaneously using two or more such polymeric reagents and catalysts are known as multipolymer reactions. A complementary extension of this concept is to use a single polymer that contains two or more different reagent and/or catalyst groups. We have developed several such polyfunctional polymeric reagents and catalysts. The scientific literature regarding multipolymer reactions and polyfunctional polymers in the context of organic synthesis was reviewed. The synthesis and application of both a monofunctional triflimide polymer and an analogous bifunctional triflimide/amine polymer were described. The monofunctional polymeric triflimide reagent was used together with an amine base to transform a series of phenols into the corresponding aryl triflates. However, the bifunctional triflimide/amine polymer was not effective in such aryl triflate synthesis. A multipolymer reaction system was presented for the selective and catalytic aerobic oxidation of primary benzylic alcohols to aldehydes. Polymer-supported 2,2'-bipyridine and 2,2,6,6-tetramethyl-piperidine-1-oxyl radical (TEMPO) were synthesized and used simultaneously as ligands for copper(II) to generate the catalytically active species required for the oxidation reactions. The recyclablility of these polymers was also examined. The synthesis of two polyfunctional polymers, one soluble and the other insoluble, were reported. Both 2,2'-bipyridine and TEMPO were attached to the same polymer backbone and these were successfully utilized in the same aerobic oxidation reactions previously performed in the multipolymer reaction system. DOI: 10.5353/th_b3970744 Subjects: Organic compounds - Synthesis Chemical reactions Polymers Catalysts