Reduction of organic compounds by lithium in low molecular weight amines. Highly selective lithium-amine reducing systems

Benkeser, Robert A.; Agnihotri, Ram K.; Burrous, Merwyn L.

doi:10.1016/s0040-4039(01)99332-3

Cited by 9 publications

(2 citation statements)

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

supporting

confidence: 86%

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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supporting

confidence: 86%

Scalable Birch reduction with lithium and ethylenediamine in tetrahydrofuran

Burrows

Kamo

Koide

2021

Science

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“…Especially, the Benkeser reduction, which is a fork of the Billups-Birch reaction [16], overcomes the drawbacks of handling ammonia when performed on kilograms or even an industrial scale [17]. But there is no mention of the corresponding alkali alkylamide salt formation in EDA or an explanation of its reactivity [18][19][20][21][22][23]. More recently, the alkylation of single-walled carbon nanotubes by lithium dissolved in EDA has been reported [24][25][26], while reduced graphene oxide is aminated [27].…”

Section: Introductionmentioning

confidence: 99%

Direct Defluorination and Amination of Polytetrafluoroethylene and Other Fluoropolymers by Lithium Alkylamides

Herlem,

Roina,

Fregnaux

et al. 2024

Molecules

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Polytetrafluoroethylene (PTFE) and, by extension, fluoropolymers are ubiquitous in science, life, and the environment as perfluoroalkyl pollutants (PFAS). In all cases, it is difficult to transform these materials due to their chemical inertness. Herein, we report a direct amination process of PTFE and some fluoropolymers such as polyvinylidene fluoride (PVDF) and Nafion by lithium alkylamide salts. Synthesizing these reactants extemporaneously between lithium metal and an aliphatic primary di- or triamine that also serves as a solvent leads to the rapid nucleophilic substitution of fluoride by an alkylamide moiety when in contact with the fluoropolymer. Moreover, lithium alkylamides dissolved in suitable solvents other than amines can react with fluoropolymers. This highly efficient one-pot process opens the way for further surface or bulk modification if needed, providing an easy, inexpensive, and fast experiment protocol on large scales.

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Δ^9,10‐Octalin

Kaiser

Benkeser

2003

Organic Syntheses

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Δ 9,10 ‐octalin solvent: 250 ml. of anhydrous ethylamine product: Δ 9,10 ‐octalin byproduct: Δ1,9‐octalin product: dimethylamine product: 1‐ tert ‐butylcyclohexene

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Reduction of organic compounds by lithium in low molecular weight amines. Highly selective lithium-amine reducing systems

Cited by 9 publications

References 1 publication

Scalable Birch reduction with lithium and ethylenediamine in tetrahydrofuran

Scalable Birch reduction with lithium and ethylenediamine in tetrahydrofuran

Direct Defluorination and Amination of Polytetrafluoroethylene and Other Fluoropolymers by Lithium Alkylamides

Δ^9,10‐Octalin

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Reduction of organic compounds by lithium in low molecular weight amines. Highly selective lithium-amine reducing systems

Cited by 9 publications

References 1 publication

Scalable Birch reduction with lithium and ethylenediamine in tetrahydrofuran

Scalable Birch reduction with lithium and ethylenediamine in tetrahydrofuran

Direct Defluorination and Amination of Polytetrafluoroethylene and Other Fluoropolymers by Lithium Alkylamides

Δ9,10‐Octalin

Contact Info

Product

Resources

About

Δ^9,10‐Octalin