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Title: Studies in modern organic chemistry : catalytic, technological and structural
Author: Hayward, J. J.
Awarding Body: University of Cambridge
Current Institution: University of Cambridge
Date of Award: 2010
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This thesis describes work done within the Ley group on a variety of projects, with a particular focus upon modern methods of synthesis. Chapter 1 initially describes work directed towards examining the use of the proline tetrazole catalyst 1.16 as a catalyst for aminations of carbonyl compounds. A novel ionic liquid-based system was developed to investigate this reaction as an oscillatory flow process. Chapter 2 gives an overview of the three enabling technologies that are of principal interest to the Ley group in general and this thesis in particular – microwave chemistry, polymer-supported reagents and flow chemistry (Fig 8888A). Chapter 3 describes the total synthesis of Siphonazole B. Our approach to this molecule was designed to make use of the enabling technologies described above, but also to evaluate them – particularly flow-based methods. With this in mind a left-hand fragment synthesis is devised and executed in the flow domain, and several approaches to the left-hand fragment investigated, culminating in the completed total synthesis. Siphonazole B is a bis­-oxazole natural product, a class of molecules that has been of interest to our group for some time. Oxazoles and other aromatic heterocycles are ubiquitous within organic chemistry, whether one considers natural products (such as the siphonazoles) or pharmaceuticals (Fig 8888B). Chapter 4 chronicles our studies towards a new synthesis of thiazolothiophenes. During the course of these studies we describe a new class of conjugated betaines (shown above) which appear to exhibit an unusual S …. S interaction in the solid state, which we have investigated crystallographically and computationally.
Supervisor: Not available Sponsor: Not available
Qualification Name: Thesis (Ph.D.) Qualification Level: Doctoral
EThOS ID:  DOI: Not available