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53
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In these experiments, both the substrate and catalyst concentration were lowered. Despite the net decrease in Cu(I) concentration, equilibrium constant calculations show that the ratio of catalyst monomer to substrate concentration increases on dilution. At sufficiently high dilution, however, the second order nature of the reduction reaction imposes a decrease in rate.
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54
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This phenomenon is often observed in reactions catalyzed by metal cluster compounds. See, for example
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0342593759
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The stereochemical preference for axial delivery of hydride represents the kinetic selectivity of the catalytic reduction: the stereoisomeric tripod-stabilized copper(I)-cis-4-tert-butylcyclohexoxide complex, generated independently by treatment of the corresponding potassium alkoxide with (tripod)CuCl, shows no stereomutation to the thermodynamically favored trans-isomer in solution at room temperature.
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The rate attenuation observed for the reduction of cyclopentanone substrates is consistent with that observed for sodium borohydride reductions of cyclopentanones versus cyclohexanones. See, for example, Ref. 36.
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68
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0343899460
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Control experiments were performed by the addition of an allyl alcohol (e.g. geraniol) to a reaction mixture of a working hydrogenation reaction, subjecting the allylic alcohol to all catalysts and catalyst-derived intermediates present during an active reduction.
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