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

被引：14

作者：

Aberg, Jenny B. ^{[1
]}

Backvall, Jan-E. ^{[1
]}

机构：

[1] Stockholm Univ, Arrhenius Lab, Dept Organ Chem, S-10691 Stockholm, Sweden

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2008年 / 14卷 / 30期

基金：

瑞典研究理事会;

关键词：

hydrogenation; reduction; ruthenium; solvent effects;

D O I：

10.1002/chem.200801195

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

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).

引用

页码：9169 / 9174

页数：6

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