The development of flow photochemical methods for the synthesis of Phenanthrenes, Helicenes and Benzochromenes

Abstract

This thesis focuses on the development of flow photochemical methods, for the synthesis of phenanthrenes, helicenes and benzochromenes. Chapter 1 reviews the literature of triplet aryl cations, which are rarely discussed intermediates in synthetic organic chemistry, which we invoke in the photochemical reactions discussed in Chapters 4 and 5. Chapters 2 and 3 are centred upon thermal and photochemical reactions of cyclobutenediones respectively. Whilst the thermal rearrangements of azidocyclobutenediones proved to be flawed for the synthesis of phenanthrenes and helicenes, we found that the photochemical rearrangements of diarylcyclobutenediones provided a useful method of synthesising phenanthrenes and helicenes fused to maleic anhydride. Chapter 4 explores the photolysis of o-iodoaryl benzyl ethers to give 6H-benzo[c]chromenes, which we show to proceed via a triplet aryl cation intermediate. In Chapter 5 this methodology is extended to the photolysis of o-iodostilbenes and bis-o-iodostilbenes to give phenanthrenes and helicenes respectively

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ORCID for David Harrowven: orcid.org/0000-0001-6730-3573

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