The Power of Solvent in Altering the Course of Photorearrangements

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Authors

ŠEBEJ Peter LIM Bum He PARK Bong Ser GIVENS Richard S. KLÁN Petr

Year of publication 2011
Type Article in Periodical
Magazine / Source Organic Letters
MU Faculty or unit

Faculty of Science

Citation
Doi http://dx.doi.org/10.1021/ol102887f
Field Organic chemistry
Keywords Photochemistry; photo-Favorskii rearrangement; water
Description 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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