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Harnessing the power of photochemistry
Photochemistry is an incredibly powerful tool for organic chemists. It enables reactions to be carried out that are impossible via standard thermal pathways. The widespread application of photochemistry is however hindered by the unpredictable yields of products obtained in reactions. One of the main causes for the low yields observed is that the products remain photoactive and thus over the course of the irradiation are consumed by secondary photoreactions. We are particularly interested in enone [2+2] photocycloadditions which enable the rapid construction of complex molecules incorporating highly strained cyclobutanes and cyclobutenes. Access to cyclobutanes is of high importance due to their presence in a number of biologically active natural products and their potential incorporation in chemotherapeutics. Furthermore the inherent strain in these four-membered rings can be exploited to provide a driving force for subsequent synthetic manipulations. We have been investigating new methodology to prevent secondary photoreactions in enone [2+2] photocycloadditions. Our approach has been to include chemical trapping agents that react selectively with the product removing the chromophore preventing further photon absorption leading to degradation. We have proven the potential of this approach by the use of a hydride reducing agent in the intramolecular photocycloaddition of 3.
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