A triphenylphosphine mediated photo-rearrangement and methanol addition of aryl chalcones to 1-propanones

Photochemical & Photobiological Sciences : Official Journal of the European Photochemistry Association and the European Society for Photobiology
Qiu SunBurkhard König

Abstract

Aryl chalcones rearrange and add methanol to give substituted propane-1-ones upon UV-A irradiation in the presence of PPh3. We propose two possible mechanisms for this photo-rearrangement. The reaction involves either the formation of a phosphine-carbonyl intermediate, nucleophilic addition of MeOH and 1,2-aryl migration or the formation of ylide and carbene intermediates. The intermediates trapped from the reaction mixture support the first mechanistic hypothesis.

References

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