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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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Cycloheptatriene is a neutral monocyclic unsaturated hydrocarbon that consists of an odd number of carbon atoms and an intervening sp3 carbon in the ring. The three double bonds in the ring correspond to 6 π electrons, which is a Huckel number, and therefore satisfies the criteria of 4n + 2 π electrons. However, the intervening sp3 carbon disrupts the continuous overlap of p orbitals. As a result, cycloheptatriene is not aromatic.
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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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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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The reductive aromatization of tridecacyclene.

Daniel P Sumy1, Aaron D Finke2, Adam C Whalley1

  • 1The University of Vermont, Department of Chemistry, Burlington, Vermont 05405, USA. Adam.Whalley@uvm.edu.

Chemical Communications (Cambridge, England)
|October 7, 2016
PubMed
Summary

Researchers synthesized the radical anion and dianion of tridecacyclene, a large polycyclic aromatic hydrocarbon. Structural analysis revealed enhanced aromaticity in the central ring of the dianion, even with its characteristic tub-like shape maintained.

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Area of Science:

  • Organic Chemistry
  • Materials Science
  • Solid-State Chemistry

Background:

  • Tridecacyclene is a large polycyclic aromatic hydrocarbon with a unique tub-like structure.
  • Understanding the electronic properties and structural modifications of polycyclic aromatic hydrocarbons upon reduction is crucial for developing new materials.

Purpose of the Study:

  • To prepare and characterize the radical anion and dianion of tridecacyclene.
  • To investigate the structural and electronic changes in tridecacyclene upon reduction.

Main Methods:

  • Reduction of tridecacyclene using potassium metal.
  • Solid-state structural analysis of the dipotassium salt of the tridecacyclene dianion using X-ray crystallography.

Main Results:

  • Successful preparation of the radical anion and dianion of tridecacyclene.
  • The crystal structure of the dipotassium salt of the dianion shows increased aromatic character in the central 8-membered ring.
  • The characteristic tub-like conformation of tridecacyclene is preserved in the dianion.

Conclusions:

  • The reduction of tridecacyclene to its dianion leads to significant electronic changes, specifically increased aromaticity.
  • Despite electronic modifications, the overall molecular geometry remains largely unchanged, preserving the tub-like structure.