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Birch reduction information


Birch reduction
Named after Arthur Birch
Reaction type Organic redox reaction
Identifiers
Organic Chemistry Portal birch-reduction
RSC ontology ID RXNO:0000042

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). Unlike catalytic hydrogenation, Birch reduction does not reduce the aromatic ring all the way to a cyclohexane.

The Birch reduction
The Birch reduction

An example is the reduction of naphthalene in ammonia and ethanol:

naphthalene Birch Reduction
naphthalene Birch Reduction

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Birch reduction

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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...

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Cycloalkene

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configurations, depending on the stereochemistry of the second ring strain. Birch reduction is a possible method to reduce reduces aromatic compounds into cycloalkenes...

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Organic redox reaction

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Organic reductions or organic oxidations or organic redox reactions are redox reactions that take place with organic compounds. In organic chemistry oxidations...

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Magnetic stirrer

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dissolving metal reductions that use an alkali metal dissolved in a primary amine, PTFE may be attacked to some extent. Birch reductions (a common dissolving...

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Aromatic compound

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dearomatization is related to hydrogenation. A classic approach is Birch reduction. The methodology is used in synthesis. Aromatic substituents: Aryl...

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Amine

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employed for the reduction of these same groups on the laboratory scale. Many amines are produced from aldehydes and ketones via reductive amination, which...

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Solvated electron

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hexamethylphosphoramide, forming blue solutions. THF dissolves alkali metal, but a Birch reduction (see § Applications) analogue does not proceed without a diamine ligand...

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Carbonyl reduction

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alkyl benzenes by catalytic hydrogenation or by Birch reduction under mild conditions. In the reduction of cyclohexanones, the hydride source can attack...

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Sodium

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organic synthesis, sodium is used in various reactions such as the Birch reduction, and the sodium fusion test is conducted to qualitatively analyse compounds...

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Anisole

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acid or boron trichloride:: 565–566  CH3OC6H5 + HI → HOC6H5 + CH3I Birch reduction of anisole gives 1-methoxycyclohexa-1,4-diene. Anisole is prepared...

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Piperidine

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C5H10NH Pyridine can also be reduced to piperidine via a modified Birch reduction using sodium in ethanol. Piperidine itself has been obtained from black...

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Benzene

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give cyclohexene or cyclohexadienes as these are superior substrates. Birch reduction, a non catalytic process, however selectively hydrogenates benzene...

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History and culture of substituted amphetamines

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with barium sulfate (Rosenmund reduction), but uses perchloric acid instead of thionyl chloride. The Birch reduction, also called the "Nazi method",...

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Pyrrole

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[citation needed] Pyrroles can undergo reductions to pyrrolidines and to pyrrolines. For example, Birch reduction of pyrrole esters and amides produced...

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Dearomatization reaction

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synthesis. Types of carbocyclic arene dearomization include hydrogenative (Birch reduction), alkylative, photochemical, thermal, oxidative, transition metal-assisted...

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Ammonia

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used in the illegal manufacture of methamphetamine through a Birch reduction. The Birch method of making methamphetamine is dangerous because the alkali...

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Cyclohexenone

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often yellow. Industrially, cyclohexenone is prepared from phenol by Birch reduction. Cyclohexenone is a ketone, or more precisely an enone. Common reactions...

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Ephedrine

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method for reducing ephedrine to methamphetamine is similar to the Birch reduction, in that it uses anhydrous ammonia and lithium metal in the reaction...

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Buckminsterfullerene

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addition with hydrogen to give polyhydrofullerenes. C60 also undergoes Birch reduction. For example, C60 reacts with lithium in liquid ammonia, followed by...

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Pyridine

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(Δ3,4)-tetrahydropyridine is obtained by electrochemical reduction of pyridine. Birch reduction converts pyridine to dihydropyridines. Pyridine is a Lewis...

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Electride

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are powerful reducing agents, as demonstrated by their use in the Birch reduction. Evaporation of these blue solutions affords a mirror of Na metal....

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John Birch Society

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The John Birch Society (JBS) is an American right-wing political advocacy group. Founded in 1958, it is anti-communist, supports social conservatism,...

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Name reaction

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such as the Pummerer rearrangement, the Pinnick oxidation and the Birch reduction are named for people other than their discoverers, but this is the...

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Outline of organic chemistry

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oxidation Reduction Birch reduction Bouveault-Blanc reduction CBS reduction Clemmensen reduction Corey-Bakshi-Shibata reduction Corey–Itsuno reduction Fukuyama...

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Cefradine

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approved by the FDA for use in the United States.[citation needed] Birch reduction of D-α-phenylglycine led to diene (2). This was N-protected using...

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List of inorganic reactions

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Arylation Aufbau reaction Barbier reaction Beta-hydride elimination Birch reduction Bönnemann cyclization Bromination Buchwald–Hartwig coupling Cadiot–Chodkiewicz...

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