Investigation of a possible solvent cage effect in the reduction of 4-aminocyclohexanone by a hydroxycyclopentadienyl ruthenium hydride |
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Authors: | Aberg Jenny B Bäckvall Jan-E |
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Institution: | Department of Organic Chemistry, Arrhenius Laboratory, Stockholm University, 106 91 Stockholm, Sweden. |
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Abstract: | No solvent cage effect could be found in the reduction of 4-aminocyclohexanone 3 by Shvo's hydroxycyclopentadienyl ruthenium hydride 2. No preference was observed in the complex formation from trapping by aminoalcohol product 4 over external trapping by aminoketone 3 or by Shvo hydride 2. A solvent cage effect has previously been proposed to support an outer-sphere mechanism in the reduction of imines by 2; this was based on the observation that there was >90% preference for complexation of the newly formed amine over an external amine. Since alcohols form stronger hydrogen bonds than amines a larger cage effect would be expected in the present study. The lack of a cage effect in the present reduction suggests that the previous results from imine reduction require an additional explanation (other than a solvent cage effect). |
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Keywords: | hydrogenation reduction ruthenium solvent effects |
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