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Birch reduction

The Birch reduction is an organic reaction that is used to convert arenes to 1,4-cyclohexadienes. The reaction is named after the Australian chemist Arthur Birch and involves the organic reduction of aromatic rings in an amine solvent (traditionally liquid ammonia) with an alkali metal (traditionally sodium) and a proton source (traditionally an alcohol). Unlike catalytic hydrogenation, Birch reduction does not reduce the aromatic ring all the way to a cyclohexane.

An example is the reduction of naphthalene in ammonia and ethanol:

Caine, D. (1976). "Reduction and Related Reactions of α,β-Unsaturated Carbonyl Compounds with Metals in Liquid Ammonia". (review). 23: 1–258. doi:10.1002/0471264180.or023.01. ISBN 0471264180.

Org. React.

 — the reducing agent

Solvated electron

 — another reaction using solvated electrons

Bouveault–Blanc reduction

 — an application

Synthesis of methamphetamine