The Power of Solvent in Altering the Course of Photorearrangements

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Issue Date
2011-02-18Author
Šebej, Peter
Lim, Bum Hee
Park, Bong Ser
Givens, Richard S.
Klán, Petr
Publisher
American Chemical Society
Type
Article
Article Version
Scholarly/refereed, author accepted manuscript
Rights
This document is the Accepted Manuscript version of a Published Work that appeared in final form in Organic Letters, copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see http://dx.doi.org/10.1021/ol102887f.
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Show full item recordAbstract
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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Citation
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
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