Novel Reduction of Various Organic Compounds with Water in the Presence of Precipitated Metals

It was found that various organic compounds were reduced in good yields by refluxing them with precipitated metals in water. Water was proved to be indispensable as a hydrogen donor. The reduction of compounds which are insoluble in water was facilitated by using a mixture of dioxane and water. It is of interest that the reduction of nitriles with this catalyst afforded the hydrochlorides of the corresponding primary amines. The results imply the participation of the chloride ion on the ppt-metal catalyst. A selective reduction of C=C was observed in some α,β-unsaturated ketones, such as mesityl oxide and 1,3-diferrocenyl-2-buten-1-one. The relative activity of the various precipitated metals depends not only upon the kinds of the metals but also upon their combination. It is assumed that the surface of the ppt-Ni is acidic as a result of the coexisting chloride ion, which might participate in the catalytic reaction.