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Acid Halides to Ketones: Gilman Reagent01:14

Acid Halides to Ketones: Gilman Reagent

2.8K
Lithium dialkyl cuprate, also known as Gilman reagents, selectively reduces acid halides to ketones. The acid chloride is treated with Gilman reagent at −78 °C in the presence of ether solution to produce a ketone in good yield.
As shown below, the mechanism proceeds in two steps. First, one of the alkyl groups of the reagent acts as a nucleophile and attacks the acyl carbon of the acid chloride to form a tetrahedral intermediate. This is followed by the reformation of the carbon–oxygen...
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Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions01:20

Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions

1.9K
Arenediazonium substitution reactions occur when the diazonium group is substituted by various functional groups such as halides, hydroxyl, nitrile, etc. For instance, arenediazonium salts react with copper(I) salts of chloride, bromide, or cyanide to form corresponding aryl chlorides, bromides, and nitriles. These reactions are named Sandmeyer reactions. Although the mechanism of this reaction is complicated, as illustrated in Figure 1, they are believed to progress via an aryl copper...
1.9K
[3,3] Sigmatropic Rearrangement of 1,5-Dienes: Cope Rearrangement01:21

[3,3] Sigmatropic Rearrangement of 1,5-Dienes: Cope Rearrangement

2.7K
The Cope rearrangement is classified as a [3,3] sigmatropic shift in 1,5-dienes, leading to a more stable, isomeric 1,5-diene. The reaction involves a concerted movement of six electrons, four from two π bonds and two from a σ bond, via an energetically favorable chair-like transition state.
2.7K
Reduction of Alkynes to trans-Alkenes: Sodium in Liquid Ammonia02:10

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

9.2K
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,...
9.2K
Diazonium Group Substitution: –OH and –H01:19

Diazonium Group Substitution: –OH and –H

2.8K
Nitrous acid, a weak acid, is prepared in situ via the reaction of sodium nitrite with a strong acid under cold conditions. This nitrous acid prepared in situ reacts with primary arylamines to form arenediazonium salts. Such reactions are known as diazotization reactions. As shown in Figure 1, the formation of arenediazonium salts begins with the decomposition of nitrous acid in an acidic solution to give nitrosonium ions.
2.8K
Molecular Geometry and Dipole Moments02:36

Molecular Geometry and Dipole Moments

13.0K
The VSEPR theory can be used to determine the electron pair geometries and molecular structures as follows:
13.0K

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[{SiNDipp}MgNa]2: A Potent Molecular Reducing Agent.

Han-Ying Liu1, Samuel E Neale1, Michael S Hill1

  • 1Department of Chemistry, University of Bath, Claverton Down, Bath BA2 7AY, U.K.

Organometallics
|April 26, 2024
PubMed
Summary
This summary is machine-generated.

A novel bimetallic compound, [{SiNDipp}MgNa]2, acts as a powerful reducing agent for various substrates. Its metal centers can cooperate or react independently, influencing reaction outcomes and ligand behavior.

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Area of Science:

  • Organometallic Chemistry
  • Main Group Chemistry
  • Redox Chemistry

Background:

  • Bimetallic compounds offer unique reactivity due to the interplay of multiple metal centers.
  • Alkaline earth metal complexes with bulky ligands are explored for novel catalytic applications.
  • Understanding cooperative effects in heterobimetallic systems is crucial for designing advanced reagents.

Purpose of the Study:

  • To synthesize and characterize the bimetallic species [{SiNDipp}MgNa]2.
  • To investigate its reducing capabilities towards various substrates.
  • To elucidate the mechanistic pathways, including cooperative and independent metal center reactivity.

Main Methods:

  • Synthesis and isolation of the bimetallic complex.
  • Redox titrations and reactions with various substrates (dioxygen, TEMPO, anthracene, benzophenone, diphenylacetylene).
  • Electron Paramagnetic Resonance (EPR) spectroscopy for reaction analysis.
  • X-ray crystallography for product characterization.
  • Computational studies (Density Functional Theory - DFT) to investigate reaction mechanisms.

Main Results:

  • The bimetallic compound [{SiNDipp}MgNa]2 demonstrates potent reducing ability, facilitating one- or two-electron reductions.
  • Reactions show evidence of cooperative behavior between the magnesium and sodium centers, as well as independent reactivity.
  • Isolation of [{SiNDipp}Mg(OCPh2)2] highlights metal-specific reactions with O-basic substrates.
  • Computational analysis reveals Mg+ → Na+ amido group migration during diphenylacetylene reduction, explaining ligand lability and macrocyclization.

Conclusions:

  • [{SiNDipp}MgNa]2 is a versatile and potent reducing agent with tunable reactivity.
  • The study reveals the intricate interplay between metal centers and the SiNDipp ligand, influencing reaction pathways.
  • Insights into ligand lability and macrocyclization provide a deeper understanding of bimetallic complex behavior.