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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).
It is of some importance in synthetic organic chemistry for the organic synthesis of new building blocks [1] and in total synthesis. [2] Types of carbocyclic arene dearomization include hydrogenative ( Birch reduction ), alkylative, photochemical, thermal, oxidative, transition metal-assisted and enzymatic.
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]
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.
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Several routes exist for the production of cyclohexenone. For the laboratory scale, it can be produced from resorcinol via 1,3-cyclohexanedione. [6] 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.
[1] [2] It was originally developed at the Royal Society of Chemistry (RSC) and is associated with the Open Biomedical Ontologies Foundry. The RXNO ontology unifies several previous attempts to systematize chemical reactions including the Merck Index and the hierarchy of Carey, Laffan, Thomson and Williams.
Here, the acid-catalyzed proton transfer first converts the cyclohexanone phenylhydrazone 1 to the intermediate 2. Subsequently, a heat-induced sigmatropic reaction occurs to produce 3 , which is protonated and cyclizes into 4 .