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This dissertation, "Development of New Polymer Supported Reagents" by Kwok-wai, Matthew, Choi, 蔡國偉, 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 NEW POLYMER SUPPORTED REAGENTS Submitted by Choi Kwok Wai Matthew for the degree of Master of Philosophy at The Universiry of Hong Kong in December 2003 The use of polymer-supported reagents has emerged as a powerful technique in organic synthesis in what is known as polymer-assisted organic synthesis. The inherent advantages of attaching reagents to insoluble supports lie in the ease of product purification, since the supports can be filtered and also because a given reaction can be driven to completion through the convenient use of excess of such reagents. Soluble polymers are alternative supports to insoluble resins for reagent delivery and this are becoming widely used. These reagents may be used to either selectively remove impurities from synthetic products or to deliver reagents to dissolved synthesis substrates A series of new polymer-supported reagents based on both non-cross- TM linked and cross-linked (JandaJel ) polystyrene were prepared and the utility of these polymers was demonstracted by their use in organic synthesis. In this thesis, the development of two new soluble polystyrene-based sulfoxide reagents for Swern oxidation reactions are introduced. i Secondly, a simplified synthesis of 4-styryldiphenylphosphine is described and used this monomer to prepare non-cross-linked polymer-supported triphenylphosphine using a homogeneous polymerization process. It is noteworthy that the 4-styryldiphenylphosphine monomer can be incorporated into the polymers at predictable levels, depending upon the ratio of monomers used in the polymerization reaction. The utility of this polymer was demonstrated by its use in Mitsunobu reactions. Thirdly, a straightforward synthesis of trityl alcohols in which one of the aryl rings is substituted with a vinyl group was presented. These compounds were used to incorporate trityl linker groups in polystyrene-based reagent supports. TM Both non-cross-linked and cross-linked (JandaJel ) polystyrene can be prepared with these monomers and these polymers are suitable as supports for solid-phase organic and peptide synthesis. Finally, a new cross-linked polystyrene-supported thioanisole reagent was reported. This reagent incorporates the flexible JandaJel cross-linker and can be treated with methyl trifluoromethanesulfonate to form the corresponding sulfonium salt. This salt in turn can be deprotonated to form a polymer-supported sulfur ylide that is able to react with carbonyl compounds to form epoxides. The thioanisole reagent can also be oxidized to form an insoluble sulfoxide reagent that is useful in Swern oxidation reactions. These reagents derived from the polymer-supported thioanisole can be recovered, regenerated, and reused. DOI: 10.5353/th_b2923052 Subjects: Polymers Supported reagents
Polymer supported chemical reactions may include those using supported substrates, reagents and catalysts, and this report describes all three types. In all cases the most frequent reason for the use of a polymeric support will be the ease of separation of the supported and the low molecular c099 species. An additional indexed section containing several hundred abstracts from the Rapra Polymer Library database provides useful references for further reading.
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
Examines recent advances in the use of polymeric reagents and catalysts with a special emphasis on new compounds, synthetic methods, and industrial processes. Brings these advances to the attention of those who are involved in organic synthesis and desire a more thorough understanding of polymers and polymeric reagents. Contains comprehensive chapters devoted to polymeric oxidizing agents, Wittig reagents, and synthesis of cross-linked polymeric templates for chiral recognition. Presents opportunities for invention and use of many new polymeric reagents and catalysts.