3,3′-Oxybispyridine and the polarographic reduction of 1,1′-dimethyl-3,3′-oxybispyridinediium diiodide

3,3′-Oxybispyridine is prepared by reaction of 3-hydroxypyridine with 3-bromopyridine and converted to the 1,1′-dimethyl diquaternary salt with methyl iodide. The salt is reduced polarographically by a one electron transfer not involving hydrogen to an unstable radical cation at a potential (E_o) of ?0.81 V in the pH range 6.3-12.0.