Samarium diiodide mediated radical cyclisations of [alpha], [beta]-unsaturated carbonyl compounds

Abstract

This thesis is concerned with the synthesis, and samarium diiodide mediated radical cyclisations of a, β-unsaturated carbonyl compounds. Particular interest is directed at the development of a range of cyclic a, β-unsaturated carbonyl systems which have been designed as mechanistic probes to elucidate the nature of the key dimerisation step in the cascade sequence towards polycyclic products. Chapter 1 presents an overview of radical chemistry, including history and key principles. A discussion on samarium diiodide chemistry is also provided, which focuses on key mechanistic aspects and the reactivity of a, β-unsaturated carbonyl compounds with the reagent. A programme of work is also discussed. Chapter 2 describes the design and synthesis of a range of cyclic a, β-unsaturated carbonyl systems, and their uses as mechanistic probes for testing the intermediacy of radical species 253 and 254 and anionic species 255. Chapter 3 depicts the development of a variety of acyclic a, β-unsaturated carbonyl systems, and their reactivity upon exposure to samarium diiodide.

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