Catalytic Reduction of 6-Bromo-1-hexene by Nickel(I) Salen Electrogenerated at Glassy Carbon Cathodes in Acetonitrile

Cyclic voltammetry and controlled-potential electrolysis have been used to characterize the catalytic reduction of 6-bromo-1-hexene by nickel(I) salen electrogenerated at a glassy carbon electrode in acetonitrile containing tetramethylammonium tetrafluoroborate. A cyclic voltammogram for the reduction of nickel(II) salen reveals the reversible one-electron process leading to formation of nickel(I) salen, whereas cyclic voltammograms for solutions containing both nickel(II) salen and 6-bromo-1-hexene provide evidence for the catalytic process. Five products (methylcyclopentane, 1-hexene, 1,2-dicyclopentylethane, 7-cyclopentylhept-1-ene, and 1,11-dodecadiene) have been separated, identified, and quantitated by means of gas chromatography and gas chromatography-mass spectrometry.