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Greener, Andrew (2025) Novel phosphoranyl and alkyliodonium reagents: structure, stability and reactivity. PhD thesis, University of Nottingham.

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Abstract

Hypervalent iodine chemistry has found many uses in organic chemistry. One of which is as surrogates for transition-metal cross-coupling reactions, introducing organic frameworks onto heteroatoms. Using this methodology is well established for aryl, vinyl and alkynyl motifs, but alkyl groups are underdeveloped in the literature, due to the low stability of hypervalent iodine complexes containing alkyl substituents.

This thesis investigates the synthesis of these alkyl-substituted hypervalent iodine species, their stability and their reactivity.

Chapter 1 introduces the background of hypervalent iodine chemistry, specifically the historical development of alkyliodonium reagents and their place within the field of alkylation chemistry.

Chapter 2 discusses introducing alkyl substituents onto cyclic, benziodoxolone motifs without any stabilising groups on the alkyl substituent.

Chapter 3 presents an investigation into the thermal stability of phosphoranyl substituted hypervalent iodine and its relationship to the structural features of the hypervalent iodine species. After this the reactivity of these species with respect to nucleophiles was studied and correlated with the thermal stability data.

Chapter 4 uses the knowledge obtained from the previous work to investigate synthetic routes to hypervalent iodine species with 2,2-difluoroethyl and phenylsulfonylmethyl substituents.

Item Type:	Thesis (University of Nottingham only) (PhD)
Supervisors:	O'Duill, Miriam
Keywords:	Heteroatoms, Alkyliodonium reagents, Hypervalent iodine. species
Subjects:	Q Science > QD Chemistry > QD241 Organic chemistry
Faculties/Schools:	UK Campuses > Faculty of Science > School of Chemistry
Item ID:	82386
Depositing User:	Greener, Andrew
Date Deposited:	12 Dec 2025 04:40
Last Modified:	12 Dec 2025 04:40
URI:	https://eprints.nottingham.ac.uk/id/eprint/82386

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