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  • 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.
  • 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. (en)
Title
  • The Power of Solvent in Altering the Course of Photorearrangements
  • The Power of Solvent in Altering the Course of Photorearrangements (en)
skos:prefLabel
  • The Power of Solvent in Altering the Course of Photorearrangements
  • The Power of Solvent in Altering the Course of Photorearrangements (en)
skos:notation
  • RIV/00216224:14310/11:00052645!RIV12-MSM-14310___
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  • P(ED0001/01/01), P(ME09021), Z(MSM0021622413)
http://linked.open...iv/cisloPeriodika
  • 4
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  • 222199
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  • RIV/00216224:14310/11:00052645
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  • Photochemistry; photo-Favorskii rearrangement; water (en)
http://linked.open.../riv/klicoveSlovo
http://linked.open...odStatuVydavatele
  • US - Spojené státy americké
http://linked.open...ontrolniKodProRIV
  • [B20768C67CB8]
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  • Organic Letters
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  • 13
http://linked.open...iv/tvurceVysledku
  • Klán, Petr
  • Givens, Richard S.
  • Lim, Bum He
  • Park, Bong Ser
  • Šebej, Peter
http://linked.open...ain/vavai/riv/wos
  • 000287122800026
http://linked.open...n/vavai/riv/zamer
issn
  • 1523-7060
number of pages
http://bibframe.org/vocab/doi
  • 10.1021/ol102887f
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  • 14310
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