It was found that Pd-carbon, Pd-asbestos, and Pd-black have high catalytic activity in the hydrogen transfer from indoline to cycloheptene. RuCl 2(PPh 3) 3, RhCl 3 · 2H 2O, IrCl 3, (NH 4) 2PdCl 4, and RhH(PPh 3) 4 also showed high activity. The hydrogen-donating ability of organic compounds in the hydrogen transfer reaction catalyzed by Pd-carbon decreased in the order: indoline > formic acid > tetrahydroquinoline > piperidine > pyrrolidine > cyclohexene > N-methylpyrrolidine > di- n-propylamine > d,l-limonene > 1,2-dihydronaphthalene, etc. Though monoenes were hydrogenated efficiently, 1,3- and 1,5-cyclooctadiene were reduced to cyclooctene in high selectivity. The initial rate of the hydrogen transfer from indoline to cycloheptene was proportional to the amine concentration at first and then became independent of the amine concentration. The rate showed a maximum when the olefin concentration was varied. This result indicates the poisoning effect of the olefin.
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