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    The Power of Solvent in Altering the Course of Photorearrangements

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    Šebej_2011.pdf (1.120Mb)
    Issue Date
    2011-02-18
    Author
    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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    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.
    URI
    http://hdl.handle.net/1808/23501
    DOI
    https://doi.org/10.1021/ol102887f
    Collections
    • Chemistry Scholarly Works [557]
    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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    Contact KU ScholarWorks
    785-864-8983
    KU Libraries
    1425 Jayhawk Blvd
    Lawrence, KS 66045
    785-864-8983

    KU Libraries
    1425 Jayhawk Blvd
    Lawrence, KS 66045
    Image Credits
     

     

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