Reduction of Organic Compounds by Lithium in Low Molecular Weight Amines. IV. The Effect of Nitro and Amino Groups on the Course of the Reduction

Benkeser, Robert A.; Lambert, Rogers F.; Ryan, Patrick W.; Stoffey, Donald G.

doi:10.1021/ja01557a030

Cited by 16 publications

(1 citation statement)

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“…This is similar to the Benkeser reduction without alcohol (Fig. 1B) (15)(16)(17)(52)(53)(54). Although the addition of an alcohol under the Benkesertype conditions gave Birch-type products (4, 18, 55), these findings have not garnered widespread use.…”

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confidence: 75%

Scalable Birch reduction with lithium and ethylenediamine in tetrahydrofuran

Burrows

Kamo

Koide

2021

Science

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Easy aryl reductions The Birch reduction has been widely used for more than half a century to achieve partial reduction of aryl rings by alkali metals at just two diametrically opposed carbon sites. However, the conditions require condensation of caustic gaseous ammonia. A variation developed soon afterward by Benkeser used safer liquid ethylene diamine but was prone to overreduction. By diluting ethylene diamine in tetrahydrofuran solvent, Burrows et al . now obtain selectivities comparable to Birch conditions but without the need for condensed ammonia. —JSY

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confidence: 75%

Scalable Birch reduction with lithium and ethylenediamine in tetrahydrofuran

Burrows

Kamo

Koide

2021

Science

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ar ‐Tetrahydro‐α‐Naphthol

Gutsche

Peter

2003

Organic Syntheses

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Benkeser Reduction

2010

Comprehensive Organic Name Reactions and Reagents

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Benkeser reduction is the reduction of aromatic and olefinic compounds with lithium or calcium to unsaturated olefins and fully reduced hydrocarbons in the presence of low molecular weight amines. It has been found that low molecular weight monoamines, particularly methylamine and ethylamine, are excellent media for reduction with lithium. The study finds that the neat monoamines, aromatic compounds are reduced to mono olefins, whereas in monoamine‐alcohol solution, di‐olefins are obtained. The Benkeser reduction in ethylenediamine frequently results in overreduction of the substrate, giving a mixture of products. This drawback has been overcome by using 1 mole of ethylenediamine or N, N ′‐dimethylethylenediamine per gram‐atom of lithium with or without the proton donor (alcohol). So far, the lithium‐reducing systems have been applied to this type of reaction. The amination to hydrocarbon has also been reported under certain conditions. The calcium‐reducing systems have also been applied extensively besides electrochemical‐reducing systems.

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Reduction of Organic Compounds by Lithium in Low Molecular Weight Amines. IV. The Effect of Nitro and Amino Groups on the Course of the Reduction

Cited by 16 publications

References 2 publications

Scalable Birch reduction with lithium and ethylenediamine in tetrahydrofuran

Scalable Birch reduction with lithium and ethylenediamine in tetrahydrofuran

ar ‐Tetrahydro‐α‐Naphthol

Benkeser Reduction

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