Organic reaction used to convert arenes to cyclohexadienes
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.
An example is the reduction of naphthalene in ammonia and ethanol:
The Birchreduction is an organic reaction that is used to convert arenes to 1,4-cyclohexadienes. The reaction is named after the Australian chemist Arthur...
configurations, depending on the stereochemistry of the second ring strain. Birchreduction is a possible method to reduce reduces aromatic compounds into cycloalkenes...
Organic reductions or organic oxidations or organic redox reactions are redox reactions that take place with organic compounds. In organic chemistry oxidations...
dissolving metal reductions that use an alkali metal dissolved in a primary amine, PTFE may be attacked to some extent. Birchreductions (a common dissolving...
dearomatization is related to hydrogenation. A classic approach is Birchreduction. The methodology is used in synthesis. Aromatic substituents: Aryl...
employed for the reduction of these same groups on the laboratory scale. Many amines are produced from aldehydes and ketones via reductive amination, which...
hexamethylphosphoramide, forming blue solutions. THF dissolves alkali metal, but a Birchreduction (see § Applications) analogue does not proceed without a diamine ligand...
alkyl benzenes by catalytic hydrogenation or by Birchreduction under mild conditions. In the reduction of cyclohexanones, the hydride source can attack...
organic synthesis, sodium is used in various reactions such as the Birchreduction, and the sodium fusion test is conducted to qualitatively analyse compounds...
C5H10NH Pyridine can also be reduced to piperidine via a modified Birchreduction using sodium in ethanol. Piperidine itself has been obtained from black...
give cyclohexene or cyclohexadienes as these are superior substrates. Birchreduction, a non catalytic process, however selectively hydrogenates benzene...
[citation needed] Pyrroles can undergo reductions to pyrrolidines and to pyrrolines. For example, Birchreduction of pyrrole esters and amides produced...
used in the illegal manufacture of methamphetamine through a Birchreduction. The Birch method of making methamphetamine is dangerous because the alkali...
often yellow. Industrially, cyclohexenone is prepared from phenol by Birchreduction. Cyclohexenone is a ketone, or more precisely an enone. Common reactions...
method for reducing ephedrine to methamphetamine is similar to the Birchreduction, in that it uses anhydrous ammonia and lithium metal in the reaction...
addition with hydrogen to give polyhydrofullerenes. C60 also undergoes Birchreduction. For example, C60 reacts with lithium in liquid ammonia, followed by...
(Δ3,4)-tetrahydropyridine is obtained by electrochemical reduction of pyridine. Birchreduction converts pyridine to dihydropyridines. Pyridine is a Lewis...
The John Birch Society (JBS) is an American right-wing political advocacy group. Founded in 1958, it is anti-communist, supports social conservatism,...