Pyridine → HCID 20358860, compound

Participants

Reaction Steps

2.65 g of 2,2'-azobis(4,5-imidazoledicarbonitrile) was placed in a flask with 65 ml of pyridine and 25 ml of galcial acetic acid. The slurry was then purged and deoxygenated thoroughly with a stream of nitrogen. Then 3 equivalents (1.95 g) of zinc dust was added. An immediate green/black solution was formed characteristic of a radical anion species. This slowly faded to a pale green as the last of the intermediate reacted. The mixture was filtered under nitrogen to remove excess zinc salts. This gave a pale yellow solution of 2,2'-hydrazobis(4,5-imidazoledicarbonitrile). Exposure of an aliquot to the air caused immediate air oxidation back to the bright yellow azo compound which precipitated as the bis pyridinium salt.

Provenance & Evidence