The power of solvent in altering the course of photorearrangements |
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Authors: | Šebej Peter Lim Bum Hee Park Bong Ser Givens Richard S Klán Petr |
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Institution: | Department of Chemistry, Faculty of Science, Masaryk University, Kamenice 5/A8, 625 00, Brno, Czech Republic. |
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Abstract: | A clean bifurcation between two important photochemical reactions through competition of a triplet state Type II H-abstraction reaction with a photo-Favorskii rearrangement for (o/p)-hydroxy-o-methylphenacyl esters that depends on the water content of the solvent has been established. The switch from the anhydrous Type II pathway that yields indanones to the aqueous-dependent pathway producing benzofuranones occurs abruptly at low water concentrations (~8%). The surprisingly clean yields suggest that such reactions are synthetically promising. |
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