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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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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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All ortho–para directors, excluding halogens, are activating groups. These groups donate electrons to the ring, making the ring carbons electron-rich. Consequently, the reactivity of the aromatic ring towards electrophilic substitution increases. For instance, the nitration of anisole is about 10,000 times faster than the nitration of benzene. The electron-donating effect of the methoxy group in anisole activates the ortho and para positions on the ring and stabilizes the corresponding...
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Simple aryl halides do not react with nucleophiles. However, nucleophilic aromatic substitutions can be forced under certain conditions, such as high temperatures or strong bases. The mechanism of substitution under such conditions involves the highly unstable and reactive benzyne intermediate. Benzyne contains equivalent carbon centers at both ends of the triple bond, each of which is equally susceptible to nucleophilic attack. This 50–50 distribution of products is...
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Radical substitution reactions can be used to remove functional groups from molecules. The hydrogenolysis of alkyl halides is one such reaction, where the weak Sn–H bond in tributyltin hydride reacts with alkyl halides to form alkanes. Here, the reagent Bu3SnH yields tributyltin halide as a byproduct.
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Hydrogen activation by an aromatic triphosphabenzene.

Lauren E Longobardi1, Christopher A Russell, Michael Green

  • 1Department of Chemistry, University of Toronto , 80 St. George Street, Toronto, Ontario, Canada M5S 3H6.

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|August 29, 2014
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Aromatic heterocycles can now be reduced without catalysts. A novel 1,3,5-triphosphabenzene undergoes direct hydrogenation, yielding unique bicyclo reduction products via a P-P bond-forming mechanism.

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Area of Science:

  • Organometallic Chemistry
  • Catalysis
  • Organic Synthesis

Background:

  • Aromatic hydrogenation typically requires harsh conditions or metal catalysts.
  • Developing milder, metal-free reduction methods is a key challenge in organic synthesis.

Purpose of the Study:

  • To investigate the direct hydrogenation of aromatic heterocycles.
  • To explore the mechanism of uncatalyzed aromatic reduction using 2,4,6-tri-tert-butyl-1,3,5-triphosphabenzene.

Main Methods:

  • Hydrogenation under mild pressure (4 atm H2).
  • Structure elucidation using X-ray crystallography and NMR spectroscopy.
  • Mechanistic studies employing para-hydrogen experiments and Density Functional Theory (DFT) calculations.

Main Results:

  • 2,4,6-tri-tert-butyl-1,3,5-triphosphabenzene is reduced to bicyclo products under 4 atm H2 without catalysts.
  • The reaction proceeds via reversible 1,4-H2 addition and an irreversible suprafacial hydride shift with P-P bond formation.
  • DFT calculations reveal facile distortion to a boat-conformation facilitates the uncatalyzed reduction.

Conclusions:

  • Direct, uncatalyzed aromatic hydrogenation is achievable using specific aromatic heterocycles.
  • The reaction mechanism involves unique conformational changes and P-P bond formation.
  • This discovery offers a new pathway for metal-free reduction of aromatic systems.