Alpha-functionalisation of carbonyl compounds

Killeen, Niall M. 2007. Alpha-functionalisation of carbonyl compounds. PhD Thesis, Cardiff University.

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Abstract

Chapter 1: Intrinsic to the methodology developed within this thesis is the exploitation of a polyheteroatom 3,3-sigmatropic rearrangement. This chapter explores the chemistry of a selection of these rearrangements in order to highlight their utility in the creation of new carbon-carbon and carbon-heteroatom bonds. Chapter 2: In this chapter the most recent advances in the alpha-functionalisation of carbonyl compounds are discussed. This review focuses mainly on organocatalyzed methodologies as these represent the forefront of current research in the field. Chapter 3: In chapter 3 the principle underlying our methodology is further described along with our results for the alpha-oxybenzoylation of cyclic, heterocyclic and acyclic ketones. Our findings for the alpha-oxybenzoylation of acetals is also described. Chapter 4: Elaboration of our family of reagents to introduce alpha-oxycarbonate and carbamate functionalities is next described with our results for a variety of reactions with cyclic and acyclic ketones. Chapter 5: Continuing expansion of our reagent family is described in chapter 5. Within this chapter our results for the alpha-oxytosylation of cyclic, acyclic and di-carbonyl compounds are presented. Chapter 6: Chapter 6 describes our attempts at synthesising a thio analogue of our reagent for the creation of a C-S bond.

Item Type:	Thesis (PhD)
Status:	Unpublished
Subjects:	Q Science > QD Chemistry
ISBN:	9781303208614
Date of First Compliant Deposit:	30 March 2016
Last Modified:	06 Nov 2024 13:36
URI:	https://orca.cardiff.ac.uk/id/eprint/56184

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