Birch Reduction

The Birch Reduction is an organic reaction which is particularly useful in synthetic organic chemistry. The reaction was reported in 1944 by the Australian chemist Arthur Birch (1915–1995) working in the Dyson Perrins Laboratory in the University of Oxford, building on earlier work by Wooster and Godfrey in 1937. It converts aromatic compounds having a benzenoid ring into a product, 1,4-cyclohexadienes, in which two hydrogen atoms have been attached on opposite ends of the molecule. It is the organic reduction of aromatic rings in liquid ammonia with sodium, lithium or potassium and an alcohol, such as ethanol and tert-butanol. This reaction is quite unlike catalytic hydrogenation, which usually reduces the aromatic ring all the way to a cyclohexane.

The original reaction reported by Arthur Birch in 1944 utilized sodium and ethanol. Subsequently A. L. Wilds noted that better yields result with lithium. Also the use of t-butyl alcohol has become common. The reaction is one of the main organic reactions utilized in all types of syntheses.

An example is the reduction of naphthalene:

Several reviews have been published.

Read more about Birch ReductionBasic Reaction Mechanism, Regioselectivity, Overall Details of The Reaction Mechanism, Reaction Regioselectivity, Underlying Mechanism of The Birch Reduction, Hückel Computations, Subsequent Literature and Varying Views, Experimental Testing and Computational Verification, Birch Reduction With Electron Withdrawing Substituents, Second Step of The Birch Reduction With Regiochemistry Giving Unconjugated Cyclohexadienes, Birch Alkylation, Modifications of The Birch Reduction

Other articles related to "birch, birch reduction, reduction":

Arthur Birch (organic Chemist)
... Arthur John Birch, AC (3 August 1915 - 8 December 1995) was an organic chemist from Australia ... Birch developed the Birch reduction of aromatic rings (by treatment with lithium metal and ammonia) which is widely used in synthetic organic chemistry ... The Birch Reduction enables the modification of steroids ...
Modifications of The Birch Reduction
... naphthalene all the way to octahydro- and decahydronaphthalene This reduction of naphthalene to isotetralin (1,4,5,8-tetrahydronaphthalene) produces some tetralin (1,2,3,4-tetrahydronaphthalene) as byproduct, as is ...

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