Khan, Ghulam Fatima (2016). Gold-catalysed reactions of alkynyl sulfoxides. University of Birmingham. M.Sc.
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Khan16MScbyRes..pdf
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Abstract
Gold π-catalysis has been used to overcome many challenges in synthesis, either by achieving complexity over few steps or providing a means to access formerly elusive functionality. This thesis details the development of a gold-catalysed reaction of alkynyl sulfoxides. The reaction of these 1,6-enynes proceeds \(via\) an intramolecular oxidative [2+1] cycloaddition. These transformations gave a range of novel, isolable thiabicyclo[3.1.0]hexanes. This previously unreported methodology gives rise to a new way of synthesising heterocycles but also proceeds \(via\) a carbenoid centre adjacent to a sulfoxide moiety – this combination of functionality is the first of its kind in acyclic systems – opening up a new class of α-carbenoid sulfoxides. The same functionality has not been achieved using classical approaches. Optimisation of the reaction was performed. The conditions were then applied to a range of alkynyl sulfoxides to explore their reaction profiles.
| Type of Work: | Thesis (Masters by Research > M.Sc.) | |||||||||
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| Award Type: | Masters by Research > M.Sc. | |||||||||
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| College/Faculty: | Colleges (2008 onwards) > College of Engineering & Physical Sciences | |||||||||
| School or Department: | School of Chemistry | |||||||||
| Funders: | None/not applicable | |||||||||
| Subjects: | Q Science > QD Chemistry | |||||||||
| URI: | http://etheses.bham.ac.uk/id/eprint/6586 |
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