Electrochemical reactions. Part X. 4-Styrylpyridine: polarography and cyclic voltammetry in dimethylformamide and reduction in protic solvents

Abstract

Polarography of 4-styrylpyridine in anhydrous dimethylformamide shows two separate one-electron waves with E_½–1·88 and –2·22 V (versus s.c.e.). Cyclic voltammetry shows the first wave to be reversible and the 4-styrylpyridine anion radical produced has a half-life of ca. 10 s at 25 °C and longer at lower temperatures. In aqueous methanol 4-styrylpyridine shows one polarographic wave. The products from electroreduction in aqueous methanol are the dihydro-derivative and meso- and (±)-2,3-diphenyl-1,4-di-(4-pyridyl)butane. The (±)-isomer was resolved. Other substituted 4-styrylpyridines give analogus products on reduction.