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Alkenes via Reductive Coupling of Aldehydes or Ketones: McMurry Reaction01:22

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The radical dimerization of ketones or aldehydes gives vicinal diols through a pinacol coupling reaction. However, the behavior of titanium metals used for the reaction as a source of electrons is unusual. When the reaction is carried out in the presence of titanium, diols can be isolated at low temperatures. Else titanium further reacts with diols, forming alkenes through the McMurry reaction.
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Vicinal Diols via Reductive Coupling of Aldehydes or Ketones: Pinacol Coupling Overview01:27

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Wilhelm Rudolph Fittig discovered the pinacol coupling reaction in 1859. It is a radical dimerization reaction and involves the reductive coupling of aldehydes or ketones in the presence of hydrocarbon solvent to yield vicinal diols.
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Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation02:24

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Introduction
Like alkenes, alkynes can be reduced to alkanes in the presence of transition metal catalysts such as Pt, Pd, or Ni. The reaction involves two sequential syn additions of hydrogen via a cis-alkene intermediate.
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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. 
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[3,3] Sigmatropic Rearrangement of Allyl Vinyl Ethers: Claisen Rearrangement01:24

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The Claisen rearrangement is a [3,3] sigmatropic rearrangement of allyl vinyl ethers to unsaturated carbonyl compounds. The rearrangement is a concerted pericyclic reaction proceeding via a chair-like transition state.
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Electrocyclic reactions are reversible reactions. They involve an intramolecular cyclization or ring-opening of a conjugated polyene. Shown below are two examples of electrocyclic reactions. In the first reaction, the formation of the cyclic product is favored. In contrast, in the second reaction, ring-opening is favored due to the high ring strain associated with cyclobutene formation.
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Catalytic Reductive Vinylidene Transfer Reactions.

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Summary
This summary is machine-generated.

Researchers developed a new catalytic reductive methylenecyclopropanation reaction using simple olefins and 1,1-dichloroalkenes. This method efficiently synthesizes strained methylenecyclopropanes, valuable synthetic intermediates.

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Area of Science:

  • Organic Chemistry
  • Catalysis
  • Synthetic Methodology

Background:

  • Methylenecyclopropanes are highly strained cyclic compounds with significant synthetic utility.
  • Their synthesis often requires specialized reagents or conditions.
  • The inherent strain energy of methylenecyclopropanes exceeds that of saturated cyclopropanes.

Purpose of the Study:

  • To develop a novel catalytic method for the synthesis of methylenecyclopropanes.
  • To utilize readily available 1,1-dichloroalkenes as precursors for vinylidene units.
  • To explore the mechanism of the catalytic reductive methylenecyclopropanation.

Main Methods:

  • Employing a dinuclear Nickel (Ni) catalyst to promote the reaction.
  • Utilizing simple olefins and 1,1-dichloroalkenes as starting materials.
  • Investigating the proposed formation of Ni2(vinylidenoid) intermediates via C-Cl oxidative addition.

Main Results:

  • Successful catalytic reductive methylenecyclopropanation of simple olefins was achieved.
  • The reaction provides efficient access to methylenecyclopropane structures.
  • The dinuclear Ni catalyst facilitates the transformation through proposed intermediates.

Conclusions:

  • A new synthetic route to methylenecyclopropanes has been established.
  • The catalytic system offers an efficient method for generating valuable synthetic intermediates.
  • The proposed mechanism involving Ni2(vinylidenoid) intermediates provides insight into the reaction pathway.