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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).
Tetrahydrofuran (THF) dissolves alkali metal, but a Birch reduction (see § Applications) analogue does not proceed without a diamine ligand. [8] Solvated electron solutions of the alkaline earth metals magnesium, calcium, strontium and barium in ethylenediamine have been used to intercalate graphite with these metals. [9]
A dearomatization reaction is an organic reaction in which the reactants are arenes and the products permanently lose their aromaticity. [1] It is of some importance in synthetic organic chemistry for the organic synthesis of new building blocks [1] and in total synthesis. [2]
Arthur John Birch, AC CMG FRS FAA (3 August 1915 – 8 December 1995) was an Australian organic chemist. [1] [2] [3] [4]Birch developed the Birch reduction of aromatic rings (by treatment with lithium metal and ammonia) which is widely used in synthetic organic chemistry.
The final step in the reduction of carboxylic acids and esters is hydrolysis of the aluminium alcoxide. [8] Esters (and amides) are more easily reduced than the parent carboxylic acids. Their reduction affords alcohols and amines, respectively. [9] The idealized equation for the reduction of an ester by lithium aluminium hydride is:
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