✦ LIBER ✦

Investigation of a Possible Solvent Cage Effect in the Reduction of 4-Aminocyclohexanone by a Hydroxycyclopentadienyl Ruthenium Hydride

✍ Scribed by Jenny B. Åberg; Jan-E. Bäckvall

Publisher: John Wiley and Sons
Year: 2008
Tongue: English
Weight: 401 KB
Volume: 14
Category: Article
ISSN: 0947-6539
DOI: 10.1002/chem.200801195

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✦ Synopsis

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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