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Investigation of a Possible Solvent Cage Effect in the Reduction of 4‐Aminocyclohexanone by a Hydroxycyclopentadienyl Ruthenium Hydride
Author(s) -
Åberg Jenny B.,
Bäckvall JanE.
Publication year - 2008
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200801195
Subject(s) - chemistry , hydride , cage , ruthenium , solvent , amine gas treating , imine , trapping , solvent effects , photochemistry , hydrogen , medicinal chemistry , organic chemistry , catalysis , ecology , mathematics , combinatorics , biology
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).