Transfer dehydrogenation of various alcohols has been investigated over het
erogeneous palladium catalysts using olefins as hydrogen acceptors. Pd/Al2O
3 together with cyclohexene is the most active and selective system, afford
ing a simple and convenient laboratory synthesis of aromatic ketones in ref
luxing cyclohexane. Hydrogenolysis-type side reactions can be suppressed by
minute amounts of a tertiary amine (selective poisoning of Pd). Aliphatic
and cycloaliphatic alcohols are barely reactive under these conditions, a d
ifference which offers the possibility of the selective transformation of a
romatic alcohols even in the presence of an aliphatic OH group.