HOMOGENEOUSLY CATALYZED HYDROGENATION OF QUINONES AND AROMATIC RADICAL CATIONS WITH ALKANES

Pentamethylbenzyl cation, dissolved in a strong proton acid, is a powerful catalyst for hydrogenation of quinones and aromatic radical ions by alkanes. The catalytic process consists of two steps, which can be studied separately. In concentrated sulfuric acid, the pentamethylbenzyl cation, for instance, reacts with alkanes yielding protonated hexamethylbenzene. In its turn protonated hexamethylbenzene transfers hydrogen to quinones or to aromatic cations with regeneration of the pentamethylbenzyl ion. © 1968.