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Title: Synthesis and reactions of aziridines via batch and flow processes
Author: Hsueh, Nathanael
ISNI:       0000 0004 6348 9990
Awarding Body: University of Warwick
Current Institution: University of Warwick
Date of Award: 2017
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This thesis describes the synthesis and ring opening reactions of aziridines performed under batch as well as continuous flow conditions. Chapter 1 gives a brief introduction to the synthesis and ring opening reactions of aziridines. Chapter 2 gives a brief introduction to flow chemistry, and describes the synthesis of aziridines from 1,2-amino alcohols, as well as their subsequent ring opening reactions. Using continuous flow methodology, various aziridines were successfully synthesized in moderate to good yields. Ring opening of these aziridines with different nucleophiles was also possible in flow. These two processes could be combined in a telescoped sequence, enabling the continuous flow synthesis of functionalized products directly from the 1,2-amino alcohols, without having to isolate the aziridine intermediates. Chapter 3 describes the aziridination of alkenes using soluble aryliminoiodanes under continuous flow. The aziridination of alkenes could be combined with further ring opening reactions via a telescoped, continuous flow process. This enabled the direct synthesis of ring opened products directly from the alkene, via in situ formed aziridines, in moderate to good yields. This second approach had broader scope than the method described in Chapter 2. Chapter 4 reports the stereocontrolled aziridinations of alkenes with different N-tosyl aryliminoiodanes. Under some conditions, the asymmetric aziridination of styrene gave different enantioselectivities when the aryl group of ArI=NTs was changed. The diastereoselective aziridination of a chromene was also briefly investigated. Chapter 5 gives a summary of the key findings, as well as possible future work. In Chapter 6, detailed experimental procedures for the work carried out in Chapters 2 – 4 are provided.
Supervisor: Not available Sponsor: Not available
Qualification Name: Thesis (Ph.D.) Qualification Level: Doctoral
EThOS ID:  DOI: Not available
Keywords: QD Chemistry