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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).
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. [9]
Cyclohexadienes, many derived from Birch reduction of aromatic compounds, form derivatives (diene)Fe(CO) 3. The affinity of the Fe(CO) 3 unit for conjugated dienes is manifested in the ability of iron carbonyls catalyse the isomerisations of 1,5-cyclooctadiene to 1,3-cyclooctadiene. Cyclohexadiene complexes undergo hydride abstraction to give ...
Although many metal-arene complexes are robust, few are prepared by the direct reaction of arenes with metal salts. The main example is provided by silver perchlorate (and related salts), which dissolve in liquid arenes and crystallize with arene ligands.
It is a colorless liquid that is used as a fragrance and flavorant. It occurs naturally but is produced by reduction of the aldehyde or carboxylic acid. [2] It reacts with hydrogen bromide to give 4-methoxylbenzyl bromide. [3]