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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).
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]
Anisole, or methoxybenzene, is an organic compound with the formula CH 3 OC 6 H 5. It is a colorless liquid with a smell reminiscent of anise seed, and in fact many of its derivatives are found in natural and artificial fragrances .
Cyclohexenone is obtained by Birch reduction of anisole followed by acid hydrolysis. It can be obtained from cyclohexanone by α-bromination followed by treatment with base. Hydrolysis of 3-chloro cyclohexene followed by oxidation of the cyclohexenol is yet another route.
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.
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.
The classical organic synthesis of this compound starts with Birch reduction of naphthalene to isotetralin, which adds dichlorocarbene (prepared in situ from chloroform and potassium tert-butoxide) to form a transannular cyclopropane ring. A second reduction then removes the chloride substituents.
The Bischler–Möhlau indole synthesis, also often referred to as the Bischler indole synthesis, [1] is a chemical reaction that forms a 2-aryl-indole from an α-bromo-acetophenone and excess aniline; it is named after August Bischler and Richard Möhlau [].
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