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Limitations of Friedel–Crafts Reactions01:26

Limitations of Friedel–Crafts Reactions

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Several restrictions limit the use of Friedel–Crafts reactions. First, the halogen in the alkyl halide must be attached to an sp3-hybridized carbon for the Friedel–Crafts reactions to occur. Vinyl or aryl halides do not react since the carbocations formed are unstable under the reaction conditions. Second, Friedel–Crafts alkylation is susceptible to carbocation rearrangement, and the major products obtained have a rearranged carbon skeleton. In contrast, the acylium ion is...
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Regioselective Formation of Enolates01:33

Regioselective Formation of Enolates

3.3K
As depicted in the figure below, the unsymmetrical ketones can form two possible enolates:  less substituted or more substituted enolates. Usually, the thermodynamic enolates are formed from the more substituted α-carbon atom, while the kinetic enolates are formed faster by deprotonation from the less substituted position. The thermodynamic enolates have lower energy, so they are  more stable. But the energy required to form kinetic enolates is less.
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Regioselectivity of Electrophilic Additions-Peroxide Effect02:35

Regioselectivity of Electrophilic Additions-Peroxide Effect

10.1K
In the presence of organic peroxides, the addition of hydrogen bromide to an alkene yields the isomer that is not predicted by Markovnikov’s rule. For example, the addition of hydrogen bromide to 2-methylpropene in the presence of peroxides gives 1-bromo-2-methylpropane. This addition reaction proceeds via a free radical mechanism, which reverses the regioselectivity. The free radical reaction mechanism involves three stages: initiation, propagation, and termination.
10.1K
Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation01:27

Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation

2.7K
Robinson annulation is a base-catalyzed reaction for the synthesis of 2-cyclohexenone derivatives from 1,3-dicarbonyl donors (such as cyclic diketones, β-ketoesters, or β-diketones) and α,β-unsaturated carbonyl acceptors. Named after Sir Robert Robinson, who discovered it, this reaction yields a six-membered ring with three new C–C bonds (two σ bonds and one π bond).
2.7K
Vicinal Diols via Reductive Coupling of Aldehydes or Ketones: Pinacol Coupling Overview01:27

Vicinal Diols via Reductive Coupling of Aldehydes or Ketones: Pinacol Coupling Overview

2.1K
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.
2.1K
Regioselectivity of Electrophilic Additions to Alkenes: Markovnikov's Rule02:17

Regioselectivity of Electrophilic Additions to Alkenes: Markovnikov's Rule

16.0K
If a set of reactants can yield multiple constitutional isomers, but one of the isomers is obtained as the major product, the reaction is said to be regioselective. In such reactions, bond formation or breaking is favored at one reaction site over others.
The hydrohalogenation of an unsymmetrical alkene can yield two haloalkane products, depending on which vinylic carbon takes up the halogen. However, one product usually predominates, where hydrogen adds to the vinylic carbon bearing the...
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Preparation of a Corannulene-functionalized Hexahelicene by CopperI-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units
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Preparation of a Corannulene-functionalized Hexahelicene by CopperI-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units

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Corannulene-Based Electron Acceptors: Combining Modular and Practical Synthesis with Electron Affinity and

Viktor Barát1, Maja Budanovic1, Si Man Tam1

  • 1Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University Singapore, 21-Nanyang Link, 637371, Singapore, Singapore.

Chemistry (Weinheim an Der Bergstrasse, Germany)
|January 25, 2020
PubMed
Summary

Researchers developed new corannulene-based electron acceptors with high electron affinity and solubility. This breakthrough offers practical accessibility for advanced material applications.

Keywords:
corannuleneelectron-deficient compoundsfused-ring systemspolycyclic aromatic hydrocarbonssulfones

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Area of Science:

  • Materials Science
  • Organic Chemistry
  • Supramolecular Chemistry

Background:

  • Corannulene derivatives are promising scaffolds for electron acceptors.
  • Achieving high electron affinity, solubility, and synthetic accessibility simultaneously remains a challenge.

Purpose of the Study:

  • To design and synthesize novel corannulene-based electron acceptors.
  • To combine high electron affinity with excellent solubility and practical synthesis.

Main Methods:

  • Incorporation of electron-withdrawing groups (imide, sulfone, trifluoromethyl) onto the corannulene core.
  • Functionalization with a long alkyl chain (C18H37) for enhanced solubility.
  • Modular three-step synthesis from a common corannulene precursor.

Main Results:

  • Successful synthesis of corannulene-based electron acceptors with high electron affinity.
  • Demonstrated high solubility in various organic solvents due to the long alkyl chain.
  • Achieved a modular synthesis with an overall isolated yield of 22-27%.

Conclusions:

  • High electron affinity, solubility, and synthetic accessibility can be achieved in corannulene-based electron acceptors.
  • The developed compounds are practical for applications requiring efficient electron acceptance.
  • The modular synthesis offers a viable route for further development and optimization.