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JOURNAL OF ORGANIC CHEMISTRY
Volume 68, Issue 20, Pages 7681-7684Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo034634a
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Kinetic studies of the ruthenium-catalyzed dehydrogenation of 1-(4-fluorophenyl)ethanol (4) by tetrafluorobenzoquinone (7) using the Shvo catalyst 1 at 70 degreesC show that the dehydrogenation by catalytic intermediate 2 is rate-determining with the rate = k[4][1](1/2) and with DeltaHdouble dagger = 17.7 kcal mol(-1) and DeltaSdouble dagger = -13.0 eu. The use of specifically deuterated derivative 4-CHOD and 4-CDOH gave individual isotope effects of k(CHOH)/k(CHOD) = 1.87 +/- 0.17 and k(CHOH)/k(CDOH) = 2.57 +/- 0.26, respectively. Dideuterated derivative 4-CDOD gave a combined isotope effect of k(CHOH)/k(CDOD) = 4.61 +/- 0.37. These isotope effects are consistent with a concerted transfer of both hydrogens of the alcohol to ruthenium species 2.
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