The addition of metallic lead and treatment with a solution of lead acetate changed the selectivity of the acticn of Ni-Al2O3 and Ni-ZnO catalysts in the hydrogenation of dienones. In the presence of a modified catalyst, hydrogen is preferentially added at the 3,4-double bond, while on an unmodified catalyst it is preferentially added at the 5,6-double bond.
Intermediate enol formation (registered by deutero-exchange) shows that the change in the direction of the process is associated with a change in its mechanism. On the modified catalyst, 1,2-addition of hydrogen is reduced, and the 3,4-bond is saturated to a substantial degree by 1,4-addition of hydrogen to the C=C C=O group.
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Borunova, N.V., Freidlin, L.K., Gvinter, L.I. et al. Change in the selectivity of the action of catalysts in the hydrogenation of the dienone group. Russ Chem Bull 21, 1254–1257 (1972). https://doi.org/10.1007/BF00854539
- Lead Acetate
- Enol Formation