Iodine → 4,4'-Bipyridine

Participants

Reaction Conditions

Reaction Steps

To 22 parts of 1-[2-pyridyl)ethyl] pyridinium chloride (obtained from pyridine and 2-vinylpyridine as in Example 13) in 100 parts of a mixture of water-acetone (1:1 v/v) was added five parts sodium cyanide, and the mixture stirred 24 hours at 25° C. The resulting dark blue solution was oxidized with an alcoholic iodine solution until the blue color disappeared and 100 parts 40% sodium hydroxide added. Cleavage of the quat and workup as in Example 15 gave 4.9 parts 4,4'-bipyridine.

Provenance & Evidence