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.
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Electronic supplementary information (ESI) available: Characterization details with NMR spectra and UV-vis spectra for supplementary information. Details of the crystal structure analysis of compound 2n. CCDC 1041821.. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c5pp00009b
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Sun, Q., Yao, C.J. & König, B. A triphenylphosphine mediated photo-rearrangement and methanol addition of aryl chalcones to 1-propanones. Photochem Photobiol Sci 14, 948–952 (2015). https://doi.org/10.1039/c5pp00009b
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DOI: https://doi.org/10.1039/c5pp00009b