A New Route to an Active Form of Nickel. Transfer Hydrogenation of Alkenes and Carbonyl Compounds with 2-Propanol

Article abstract of DOI:10.1021/jo00217a014

A new procedure for the transfer hydrogenation of alkenes and carbonyl compounds have been developed using an activated form of metallic nickel prepared by the thermal decomposition of nickel diisopropoxide in boiling 2-propanol.Monosubstituted alkenes undergo carbon-carbon double-bond migration more quickly than reduction; the 2-alkene produced is then reduced to alkane.Ketones are reduced in high yields, provided that acetone formed during the process is removed continuously.Unsaturated ketones are first converted to saturated ketones andthen to alcohols, so by a careful control of the reaction course it is possible to stop the reaction at the first stage.Finally a comparison with the transfer hydrogenation of ketones, catalyzed by alkali metal isopropoxides in 2-propanol, has been performed.