Electrolytic reduction of 3-cyanoquinoline

✍ Scribed by D.N. Schluter; T. Biegler; E.V. Brown; H.H. Bauer

• Publisher: Elsevier Science
• Year: 1976
• Tongue: English
• Weight: 409 KB
• Volume: 21
• Category: Article
• ISSN: 0013-4686
• DOI: 10.1016/0013-4686(76)85006-2

✦ Synopsis

Two well-defined one-electron waves are observed on the polarograms for the reduction of 3-cyanoquinoline in 9S"/" ethanol containing 1M ammonium acetate. During macroscale electrolysis at a potential on the plateau of either wave, the ratio of the wave-heights remains unity. Polarographic and voltammetric evidence is presented for a mechanism in which the first wave represents a reversible one-electron reduction to a radical which then rapidly dimerizes. The second wave represents an irreversible one-electron reduction of the initially formed radical. The reduction mechanism suggested by the electrochemical evidence is verified by the isolation of dimeric products from controlled-potential electrolysis at the top of the first wave and the isolation of 1,4-dihydro-3-cyanoquinoline at the top of the second wave. The chemical characteristics of the dirneric products and the two-electron reaction product are discussed.