Investigating the reactivity of a-oxo gold metal carbenoids formed from ynamides

Priest, Joshua Duncan (2017). Investigating the reactivity of a-oxo gold metal carbenoids formed from ynamides. University of Birmingham. Ph.D.

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The work presented in this thesis focusses upon the use of α-oxo gold carbene species formed from the intermolecular oxidation of ynamides, and their application as alternatives to diazo compounds in carbene chemistry. Throughout this work the use of ynamides has allowed production of α-oxo gold carbene species that would be either unobtainable or difficult to produce through dediazotisation chemistry. Allowing for the synthesis of novel compounds while avoiding the impractical or hazardous chemistry that would be necessary to produce the equivalent diazo compounds. The use of α-oxo gold carbenes in the synthesis of novel compounds in intramolecular Buchner reactions, the initial difficulties encountered and investigation of how carbene character and substrate choice affects the product selectivity observed in these reactions is described. Examination of the [2,3]-sigmatropic rearrangements of sulfonium ylides, formed from gold catalysed ynamide oxidation, and the effects of ynamide and sulfide variation upon the atypically high diastereoselectivity observed are described and discussed. A range of novel products has been produced and efforts towards their derivatisation described.

Type of Work: Thesis (Doctorates > Ph.D.)
Award Type: Doctorates > Ph.D.
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


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