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Synthesis and Reactions of Novel Oxindoles

Edeson, Steven (2015) Synthesis and Reactions of Novel Oxindoles. PhD thesis, University of Sheffield.

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Abstract

An important issue with the assignment of E/Z alkene geometry of 3-acylidene-oxindoles was addressed. A novel UV/Visible spectroscopic assay was developed in order to achieve this, taking advantage of contrasting electronic properties for different E/Z isomer sets. Moreover, a novel acylidene oxindole was prepared and used to provide further supporting evidence for this spectroscopic assay. Finally, the stability of related E/Z isomers was investigated, and indicated facile isomerisation to a thermodynamic minimum. A copper promoted cyclisation of o-nitrophenyl iodoacetylenes to 2-iodoisatogens was discovered. These compounds were applicable as precursors to novel isatins and consequently 3-acylidene oxindoles. The metal free aryl and alkyl cross coupling reactions of 2-iodoisatogens was developed, providing a divergent synthetic strategy to the medicinally relevant isatogen molecular group. Furthermore, an unprecedented isatogen mode of reactivity was discovered affording pseudoindoxyls, a privileged class of molecule. The mechanism for this transformation was proposed, based on control reactions and strong literature precedent.

Item Type: Thesis (PhD)
Academic Units: The University of Sheffield > Faculty of Science (Sheffield) > Chemistry (Sheffield)
Identification Number/EthosID: uk.bl.ethos.680579
Depositing User: Dr Steven Edeson
Date Deposited: 15 Mar 2016 13:24
Last Modified: 25 Sep 2019 20:01
URI: http://etheses.whiterose.ac.uk/id/eprint/12114

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