The Birch reduction is an organic reaction where aromatic rings undergo a 1,4-reduction to provide unconjugated cyclohexadienes. 1262412-13-4 web The reduction is conducted by sodium or lithium metal in liquid ammonia and in the presence of an alcohol. Buy6-Chloro-2-fluoro-3-iodopyridine The mechanism begins with a single electron transfer(SET) from the metal to the aromatic ring, forming a radical anion. The anion then picks up a proton from the alcohol which results in a neutral radical intermediate. Another SET, and abstraction of a proton from the alcohol results in the final cyclohexadiene product and two equivalents of metal alkoxide salt as a byproduct. In the case of substituted aromatic rings, the regiochemistry can be predicted using Birch’s empirical rules. ^[1]