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Related Concept Videos

Nucleophilic Aromatic Substitution: Elimination–Addition01:11

Nucleophilic Aromatic Substitution: Elimination–Addition

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 confirmed through isotopic...
ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH301:11

ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH3

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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Cycloaddition Reactions: MO Requirements for Photochemical Activation01:12

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Directing Effect of Substituents: meta-Directing Groups

Substituents on the benzene ring that direct an incoming electrophile to undergo substitution at the meta position are called meta directors. All meta directors either have a positive charge on the atom directly bonded to the ring or a partial positive charge. These groups function by withdrawing electrons from the ring through inductive and resonance effects. Consider the carbocation intermediates formed upon the addition of an electrophile on nitrobenzene at the ortho, meta, and para...

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Preparation of a Corannulene-functionalized Hexahelicene by Copper(I)-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units
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Optically active calixarenes conduced by methylene substitution.

Vijay Gopalsamuthiram1, Alexander V Predeus, Rui H Huang

  • 1Department of Chemistry, Michigan State University, East Lansing, Michigan 48824, USA.

Journal of the American Chemical Society
|November 26, 2009
PubMed
Summary

Researchers developed a novel synthesis for optically active calix[4]arenes, creating chirality via methylene bridge substitution. This method utilizes a key triple annulation reaction for efficient macrocycle construction.

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Published on: April 1, 2013

Area of Science:

  • Organic Chemistry
  • Supramolecular Chemistry
  • Asymmetric Synthesis

Background:

  • Calix[4]arenes are macrocyclic compounds with diverse applications.
  • Chirality in calix[4]arenes is typically achieved through substituents on the aromatic rings or the upper/lower rims.
  • Developing methods for chirality originating from the methylene bridges is an underexplored area.

Purpose of the Study:

  • To describe the first synthetic method for optically active calix[4]arenes chiral due to substitution on the methylene bridges.
  • To demonstrate a novel triple annulation reaction for calixarene synthesis.
  • To showcase the stereoselective synthesis of diastereomers.

Main Methods:

  • A key step involves the reaction of a biscarbene complex with a diyne.
  • This reaction forms two benzene rings and the macrocyclic ring in a single transformation.
  • Stereoselective synthesis is achieved by controlling the absolute configurations of precursors.

Main Results:

  • The synthesis of optically active calix[4]arenes with chirality at the methylene bridges was achieved.
  • The triple annulation process was successfully applied to synthesize di- and tetramethoxycalix[4]arenes.
  • Two diastereomers of tetramethoxycalix[4]arenes were synthesized stereoselectively.

Conclusions:

  • A novel and flexible synthetic route to optically active calix[4]arenes has been established.
  • The described method provides access to chiral calix[4]arenes with unique substitution patterns.
  • This work opens new avenues for designing chiral macrocyclic hosts.