Stereochemistry on the Catalytic Hydrogenation of 1-t-Butyl-4-methylenecyclohexane over Modified Raney Ni, Co, and Fe Catalysts

Contrary to a fresh catalyst, aged Raney Ni in ethanol provided exclusively a less stable product in the hydrogenation of the title compound. A similar stereoselectivity was observed over a catalyst which was refluxed in ethanol as well as that treated with carbon monoxide. These results indicate that the catalyst stored in ethanol is modified with carbon monoxide generated by the decomposition of the solvent.