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Synthesis and applications of polymer supported peracids

In recent years, polymer-assisted solution-phase synthesis has become a prevalent method because of its various advantages over conventional solution-phase chemistry, such as the ease of separation of the supported species from a reaction mixture by filtration and washing, the opportunity to use an excess of the reagent to force the reaction to completion, and the adaptability to continuous-flow processes. Peroxycarboxylic acids are common oxidants in a wide range of chemical transformations, but their use is often limited because of the associated handling risks. Some relatively stable peracids, such as <i>meta</i>-chloroperoxybenzoic acid, are commercially available, but quenching of unreacted species followed by extractions and/or chromatography separation is often required. The immobilisation of this type of reagent on a solid support can offer distinct advantages with respect to handling and stability. Carboxylic ion-exchange resins, such as acrylic macroporous matrix, can be oxidised to give highly functionalised supported peroxycarboxylic acids. The polymer-supported peracid generated from Dowex MAC-3<sup>®</sup> proved to be the best in terms of oxidation capacity among the supports and reaction conditions tested. The new high-loading polymer-supported peracid was stable under standard laboratory practice, also when it was crushed or heated, and it was used successfully in the oxidation of sulfides, alkenes, and pyridines, giving the products with high yields and purities without the need for any additional purification step.
Date January 2009
CreatorsSechi, Gianluca
PublisherUniversity of Edinburgh
Source SetsEthos UK
Detected LanguageEnglish
TypeElectronic Thesis or Dissertation

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