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The Power of Solvent in Altering the Course of Photorearrangements
Šebej, Peter Lim, Bum Hee Park, Bong Ser Givens, Richard S. Klán, Petr
Šebej, Peter
Lim, Bum Hee
Park, Bong Ser
Givens, Richard S.
Klán, Petr
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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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2011-02-18
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American Chemical Society
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Šebej, P., Lim, B. H., Park, B. S., Givens, R. S., & Klán, P. (2011). The Power of Solvent in Altering the Course of Photorearrangements. Organic Letters, 13(4), 644–647. http://doi.org/10.1021/ol102887f