Metal-Catalysed Reactions of Hydrocarbons / 10-Hydrogenation of the Aromatic Ring

HYDROGENATION OF THE AROMATIC RING

467

Scheme 10.5. Structures of polycyclic aromatic hydrocarbons.

behaves similarly. With fluoranthene, the sequence is 2 . . . 1 . . . 3; with chrysene it is 1 . . . 2 . . . 4, the final product containing a CC bond between rings 2 and 3. In the case of perylene, the sequence is 1,4, then 2, 3, the central ring retaining aromatic character. The middle rings in rubicene and decacyclene not surprisingly resisted reduction. More recently the reduction of some of these molecules has been studied using noble metals supported on carbon or alumina. Rhodium and palladium were the most active, and the relative ease of reducing the various rings was said to be governed by the LUMO electron density, the π -bond order and the stability of the product.119

468	CHAPTER 10

The grandfather of all fused ring systems must be buckminsterfullerene, C60, the structure of which is too well known to need depiction: with Ni/Al2O3 at 323–423 K it is hydrogenated to C60H36, no lighter hydrocarbons being formed.120 Reduction occurs faster than that of toluene. This paper gives references to previous work with noble metals. The use of C60H36 as a means of hydrogen storage has been suggested.121

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FURTHER READING

Temperature inversion of the rate of benzene hydrogenation Pt 29, 38, 46, 48, 51, 54, 55, 56, 58

Pd 16, 30, 34, 55, 58

Ni 4, 5, 33, 50, 53, 59, 60 Ru 16, 61

Ru, Fe 16 Co 31 Cu 62