Mechanohydrogenation

Article abstract of DOI:10.1016/S0040-4039(97)10463-4

Treatment of naphthalene and biphenyl with alumina and hydrogen in a vibratory mill for about 5h at ambient temperature gives up to 75% and 15% of tetralin and phenylcyclohexane respectively. This suggests that the previously reported disproportionation of naphthalene and biphenyl to give tetralin and phenylcyclohexane by analogous treatment under nitrogen proceeds at least partially by a step involving molecular hydrogen. However, these observations are not general because identical mechanical treatment of trans- stilbene under hydrogen gave less bibenzyl than under nitrogen.