Photooxidation of Fulvenes in a Continuous Flow Photoreactor using Carbon Dioxide as a Solvent

Lingqiao Wu, Darren S. Lee, Hamza Boufroura, Martyn Poliakoff, Michael W. George

Research output: Journal PublicationArticlepeer-review

6 Citations (Scopus)

Abstract

A range of 3-substituted oxepinones have been synthesised by the photooxidation of fulvenes with photochemically generated singlet oxygen (1O2) using carbon dioxide (CO2) as a solvent and a CO2-soluble porphyrin photosensitizer. The reactive intermediates generated in this reaction decompose to yield a range of useful and underutilized building blocks that are not easily accessible using more traditional reaction setups. Fulvenes containing an exocyclic allylic hydrogen are shown to form three products through potentially competing intramolecular pathways, which can be tuned to some extent by adjusting the conditions in the flow reactor. A range of substrates containing a variety of functional groups was examined; this led to lower yields of the desired lactones being observed in the case of compounds containing polar electron-donating groups. We also demonstrate that one of the lactones can be further hydrogenated over a Pd/C catalyst to the unsaturated 7-membered ring in high yield.

Original languageEnglish
Pages (from-to)580-585
Number of pages6
JournalChemPhotoChem
Volume2
Issue number7
DOIs
Publication statusPublished - 1 Jul 2018

Keywords

  • flow chemistry
  • fulvenes
  • photooxidation
  • singlet oxygen
  • supercritical carbon dioxide

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Analytical Chemistry

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