ELECTROCHEMICAL REDUCTION OF 2-CYANO-1-METHYLPYRIDINIUM ION

2-Cyano-1-methylpyridinium ion, I, exhibits three well-defined polarographic waves in Britton-Robinson buffer at pH 5 to 8. Electrolysis at the plateau potential of the most positive wave, involving a one-electron uptake, leads to the formation of a pyridinyl radical which probably dimerizes to a 2,4′-linked structure, VIII. Electrolysis at the plateau potential of the second wave, involving a number of electrons variable between nearly 4 (at pH≈5) and ≈3 (at pH≈8), leads to the formation of a mixture of 2-aminomethyl-1-methylpyridinium ion and 1-methylpyridinium ion. At the third wave potentials the second wave products are further reduced to give basic species with catalytic activity. © 1979 Elsevier Sequoia S.A.