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Studying the synthesis and reactivity of sulfonium ylides derived via gold catalysts

Baker, Thomas (2014)
Ph.D. thesis, University of Birmingham.

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This thesis details the development of a gold-catalysed, ketone-stabilised ylide synthesis and the intermolecular reaction of this ylide. The reaction of this ylide with butenone proceeds via a novel, three-component coupling. This represents the first intermolecular reaction of a gold-derived ylide.

The development of a novel, gold-catalysed, amide-stabilised ylide synthesis was also successful. The ylides underwent 2,3-sigmatropic rearrangements and Stevens 1,2-shifts. The Stevens rearrangement has previously not been reported for gold-derived ylides. These ylide transformations gave a range of novel, polysubstituted thiomorpholinones, which are difficult to access via classical approaches. The amide-stabilised ylides were found to be unsuitable for intermolecular reaction.

Thioynol ethers were also investigated as triple-bonded substrates for gold-catalysed reactions. While the thioynol ethers were found to be significantly less reactive than the equivalent alkyne or ynamide, it was possible employ them for the synthesis of oxazoles in comparable yield to ynol ethers.

Type of Work:Ph.D. thesis.
Supervisor(s):Davies, Paul and Simpkins, N. S.
School/Faculty:Colleges (2008 onwards) > College of Engineering & Physical Sciences
Department:School of Chemistry
Subjects:QD Chemistry
Institution:University of Birmingham
ID Code:5291
This unpublished thesis/dissertation is copyright of the author and/or third parties. The intellectual property rights of the author or third parties in respect of this work are as defined by The Copyright Designs and Patents Act 1988 or as modified by any successor legislation. Any use made of information contained in this thesis/dissertation must be in accordance with that legislation and must be properly acknowledged. Further distribution or reproduction in any format is prohibited without the permission of the copyright holder.
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