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Benzene to 1,4-Cyclohexadiene: Birch Reduction Mechanism01:18

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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...
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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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Reduction of Alkenes: Asymmetric Catalytic Hydrogenation02:17

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Catalytic hydrogenation of alkenes is a transition-metal catalyzed reduction of the double bond using molecular hydrogen to give alkanes. The mode of hydrogen addition follows syn stereochemistry.
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Reduction of Benzene to Cyclohexane: Catalytic Hydrogenation01:28

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Unlike the easy catalytic hydrogenation of an alkene double bond, hydrogenation of a benzene double bond under similar reaction conditions does not take place easily. For example, in the reduction of stilbene, the benzene ring remains unaffected while the alkene bond gets reduced. Hydrogenation of an alkene double bond is exothermic and a favorable process. In contrast, to hydrogenate the first unsaturated bond of benzene, an energy input is needed; that is, the process is endothermic. This is...
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Recently, the development of olefin metathesis polymerization advanced the field of polymer synthesis. Simply put, the reorganization of substituents on their double bonds between two olefins in the presence of a catalyst is known as the olefin metathesis reaction. The use of metathesis reaction for polymer synthesis is called olefin metathesis polymerization.
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Some cycloaddition reactions are activated by heat, while others are initiated by light. For example, a [2 + 2] cycloaddition between two ethylene molecules occurs only in the presence of light. It is photochemically allowed but thermally forbidden.
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CO Reduction to Ethylene and Cyclopropane via a Trappable Ruthenium Methylidene.

Allison M Smith1, Stephen J Tereniak1, Haley Cox2

  • 1Department of Chemistry, University of North Carolina at Chapel Hill, 125 South Road, Chapel Hill, North Carolina 27599-3290, United States.

Journal of the American Chemical Society
|October 7, 2025
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Summary

Ruthenium catalysts can now convert carbon monoxide into multicarbon products like ethylene and cyclopropane, overcoming previous limitations in C-C bond formation for CO reduction.

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Area of Science:

  • Organometallic Chemistry
  • Catalysis
  • Carbon Chemistry

Background:

  • Ruthenium complexes like cis-[Ru(bpy)2(CO)2]2+ reduce CO2 and CO to C1 products.
  • Forming C-C bonds from CO has been a significant challenge in catalysis.

Purpose of the Study:

  • To present a novel reaction pathway for converting carbon monoxide (CO) into multicarbon products.
  • To elucidate the key intermediates involved in C-C bond formation during CO conversion.

Main Methods:

  • Investigated the protonolysis of a ruthenium hydroxymethyl complex.
  • Utilized trapping experiments with nitriles and pyridine to characterize key intermediates.
  • Employed crystallographic analysis to determine the structure of an ylide complex.

Main Results:

  • A ruthenium methylidene complex, [Ru(bpy')2(CO)(CH2)]2+, was identified as a key intermediate.
  • Ethylene was generated from the methylidene complex via protonolysis of the hydroxymethyl precursor.
  • Demonstrated C-C bond formation through the reaction of the methylidene intermediate with nitriles, pyridine, and even ethylene, leading to cyclopropane.

Conclusions:

  • Developed a new pathway for CO conversion to multicarbon products (ethylene, cyclopropane).
  • Identified and characterized a reactive methylidene intermediate crucial for C-C bond formation.
  • Findings offer insights for designing improved CO and CO2 reduction catalysts.