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Aldehydes and ketones form enols, although only about 1% of the enol is present at the equilibrium for simple monocarbonyl compounds. The enol form is undetectable for acetaldehyde, present as only 1.5 × 10−4 % of acetone, and present as only 1.2% of cyclohexanone. Two kinds of regioisomeric enols are possible for unsymmetrical ketones, and their net composition is 1% at equilibrium. This instability is due to the lower bond energy of C=C than the C=O group. The additional...
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Acetoacetic ester synthesis is a method to obtain ketones from alkyl halides and β-keto esters. The reaction occurs in the presence of an alkoxide base that abstracts the acidic proton of the β-keto esters. The step results in an enolate ion which is doubly stabilized. The enolate then reacts with an alkyl halide via the SN2 process to produce an alkylated ester intermediate with a new C–C bond. The hydrolysis of the intermediate, followed by acidification, results in an...
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A new class of customisable stable boronic ester assemblies.

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Researchers developed a customizable method for creating covalent macrocycles and cages using polynorbornane bis-diols and boronic acids. The resulting structures exhibit excellent stability and resistance to hydrolysis, offering versatile applications in materials science.

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Area of Science:

  • Organic Chemistry
  • Supramolecular Chemistry
  • Materials Science

Background:

  • Covalent macrocycles and cages are important supramolecular structures.
  • Developing efficient and customizable synthesis methods is crucial for their application.
  • Polynorbornane frameworks offer unique structural properties.

Purpose of the Study:

  • To develop a novel, adaptable strategy for synthesizing covalent macrocycles and cages.
  • To explore the use of fused polynorbornane-based bis-diols and boronic acids for construct assembly.
  • To evaluate the stability and hydrolytic resistance of the synthesized architectures.

Main Methods:

  • Reaction between fused polynorbornane-based bis-diols and commercially available boronic acids.
  • Customization of bis-diol length and dihedral angles (90° and 180°).
  • Combination with di- or triboronic acids to form various architectures.

Main Results:

  • An efficient and customizable method for assembling covalent macrocycles and cages was established.
  • Access to a range of architectures was achieved by varying bis-diol and boronic acid components.
  • The resulting constructs demonstrated significant resistance to hydrolysis, even after 24-hour exposure to dilute acetic or trifluoroacetic acid.

Conclusions:

  • The developed approach provides a versatile platform for the rational design and synthesis of complex covalent architectures.
  • The hydrolytic stability of the constructs suggests potential for applications in demanding environments.
  • This method offers a customizable route to novel macrocyclic and cage compounds.