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Reduction of Alkynes to trans-Alkenes: Sodium in Liquid Ammonia02:10

Reduction of Alkynes to trans-Alkenes: Sodium in Liquid Ammonia

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Alkynes can be reduced to trans-alkenes using sodium or lithium in liquid ammonia. The reaction, known as dissolving metal reduction, proceeds with an anti addition of hydrogen across the carbon–carbon triple bond to form the trans product. Since ammonia exists as a gas (bp = −33°C) at room temperature, the reaction is carried out at low temperatures using a mixture of dry ice (sublimes at −78°C) and acetone. 
When dissolved in liquid ammonia, an alkali metal, such as sodium,...
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Alcohols from Carbonyl Compounds: Reduction02:23

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Reduction is a simple strategy to convert a carbonyl group to a hydroxyl group. The three major pathways to reduce carbonyls to alcohols are catalytic hydrogenation, hydride reduction, and borane reduction.
Catalytic hydrogenation is similar to the reduction of an alkene or alkyne by adding H2 across the pi bond in the presence of transition metal catalysts like Raney Ni, Pd–C, Pt, or Ru. Aldehydes and ketones can be reduced by this method, often under mild to moderate heat (25–100°C) and...
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Benzene to 1,4-Cyclohexadiene: Birch Reduction Mechanism01:18

Benzene to 1,4-Cyclohexadiene: Birch Reduction Mechanism

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Birch reduction uses solvated electrons as reducing agents. The reaction converts benzene to 1,4-cyclohexadiene. The reaction proceeds by the transfer of a single electron to the ring to form a benzene radical anion. This anion is highly basic—it abstracts a proton from the alcohol to form a cyclohexadienyl radical. Another single electron transfer gives the cyclohexadienyl anion. A proton transfer from the alcohol forms 1,4-cyclohexadiene. Since this reduction occurs via radical anion...
2.4K
Nitriles to Amines: LiAlH4 Reduction00:55

Nitriles to Amines: LiAlH4 Reduction

4.1K
Nitriles are reduced to amines in the presence of strong reducing agents like lithium aluminum hydride through a typical nucleophilic acyl substitution. The reaction requires two equivalents of the reducing agent. The reducing agent acts as a source of hydride ions.
As shown below, the mechanism involves three steps. Firstly, the hydride ion acting as a nucleophile attacks the nitrile carbon to form an anion. In the second step, a second equivalent of the hydride ion attacks the anion to...
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Radical Substitution: Allylic Bromination01:27

Radical Substitution: Allylic Bromination

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In organic synthesis, the formation of products can be altered by changing the reaction conditions. For example, a dibromo addition product is formed when propene is treated with bromine at room temperature. In contrast, propene undergoes allylic substitution in non-polar solvents at high temperatures to give 3-bromopropene. In order to avoid the addition reaction, the bromine concentration must be kept as low as possible throughout the reaction. This can be achieved using N-bromosuccinimide...
5.9K
Preparation of Amines: Reduction of Oximes and Nitro Compounds01:29

Preparation of Amines: Reduction of Oximes and Nitro Compounds

4.2K
Oximes can be reduced to primary amines using catalytic hydrogenation, hydride reduction, or sodium metal reduction. The reduction of aliphatic and aromatic nitro compounds to primary amines takes place by either catalytic hydrogenation or by using active metals like Fe, Zn, and Sn in the presence of an acid.
Though catalytic hydrogenation can reduce nitrobenzenes, the reduction is nonselective in the presence of other functional groups. For instance, if nitrobenzene contains an aldehyde group,...
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Nitroalkene reduction in deep eutectic solvents promoted by BH3NH3.

Chiara Faverio1, Monica Fiorenza Boselli1, Patricia Camarero Gonzalez1

  • 1Dipartimento di Chimica, Università degli Studi di Milano, Via C. Golgi, 19, I-20133, Milano, Italy.

Beilstein Journal of Organic Chemistry
|May 24, 2021
PubMed
Summary

Deep eutectic solvents (DESs) offer a green alternative for synthesizing nitroalkanes from nitroalkenes using a convenient reagent. This sustainable method simplifies product isolation and allows for solvent recycling.

Keywords:
DESalternative solventsatom economynitro derivativesreduction

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Area of Science:

  • Green chemistry and sustainable synthesis.
  • Organic synthesis and catalysis.
  • Biorenewable materials and solvents.

Background:

  • Traditional organic solvents pose environmental and safety concerns.
  • Deep eutectic solvents (DESs) are emerging as sustainable alternatives.
  • Nitroalkanes are key precursors for synthesizing valuable amine compounds.

Purpose of the Study:

  • To develop a green and sustainable method for nitroalkane synthesis.
  • To utilize bio-based deep eutectic solvents (DESs) with an atom-economic reagent.
  • To establish a solvent-free isolation protocol and investigate DES recyclability.

Main Methods:

  • Chemoselective reduction of various nitrostyrenes and nitroalkenes.
  • Utilizing borane-ammonia (BH3NH3) as the reducing agent.
  • Employing bio-based deep eutectic mixtures as reaction media.

Main Results:

  • Successful synthesis of nitroalkanes from diverse nitroalkenes.
  • High chemoselectivity achieved in the reduction process.
  • Development of a reproducible, solvent-free product isolation procedure.
  • Demonstrated recyclability of the deep eutectic solvent mixture.

Conclusions:

  • The developed method offers an efficient, green, and sustainable route to nitroalkanes.
  • Bio-based DESs combined with BH3NH3 provide a viable alternative to traditional organic solvents.
  • The protocol facilitates environmentally friendly chemical synthesis and product purification.