The Photochemistry of Conjugated Enolates

Student thesis: Doctoral ThesisDoctor of Philosophy (PhD)

Abstract

This thesis investigates the novel photochemical reactivity of conjugated enolates, transforming their conventional role as thermally reactive intermediates into photochemically active species that enable a range of unique synthetic transformations. This thesis focuses on the exploration of the photochemical ring-contraction and migration of both five- and six-membered lactam enolates, revealing efficient pathways for synthesising highly substituted cyclopropanes and cyclobutanes under mild irradiation conditions. Overall, this thesis expands the understanding of enolate chemistry by exploiting their intrinsic chromophore, presenting a range of innovative photochemical transformations.
Date of Award10 Dec 2024
Original languageEnglish
Awarding Institution
  • University of Bristol
SupervisorAndrew J Orr-Ewing (Supervisor) & Jonathan Clayden (Supervisor)

Keywords

  • Photochemistry
  • Synthesis
  • Organolithium
  • Enolate
  • Rearrangement reaction
  • Ring Opening
  • Ring-Contraction
  • Amide
  • Conjugation

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