Publication details

The Power of Solvent in Altering the Course of Photorearrangements

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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