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Alkylation of β-Diester Enolates: Malonic Ester Synthesis01:14

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Malonic ester synthesis is a method to obtain α substituted carboxylic acids from ꞵ-diesters such as diethyl malonate and alkyl halides.
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Cycloaddition Reactions: Overview01:16

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Cycloadditions are one of the most valuable and effective synthesis routes to form cyclic compounds. These are concerted pericyclic reactions between two unsaturated compounds resulting in a cyclic product with two new σ bonds formed at the expense of π bonds. The [4 + 2] cycloaddition, known as the Diels–Alder reaction, is the most common. The other example is a [2 + 2] cycloaddition.
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Thermal cycloadditions are reactions where the source of activation energy needed to initiate the reaction is provided in the form of heat. A typical example of a thermally-allowed cycloaddition is the Diels–Alder reaction, which is a [4 + 2] cycloaddition. In contrast, a [2 + 2] cycloaddition is thermally forbidden.
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Stability of Substituted Cyclohexanes02:30

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This lesson discusses the stability of substituted cyclohexanes with a focus on energies of various conformers and the effect of 1,3-diaxial interactions.
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For example, in...

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Synthesis, Structural Characterization and Reactivity of Macrocyclic Cyclo[2]malonates.

Samuele Ruffoli1, Andrea Vitale1, Kevin D'Addazio1

  • 1Dipartimento di Chimica Giacomo CiamicianCiamician and INSTM Research Unit, Università di Bologna, Via Piero Gobetti, 85, 40129 Bologna, Italy.

ACS Omega
|June 29, 2026
PubMed
Summary
This summary is machine-generated.

Researchers synthesized novel oxygen-bridged cyclo[2]-malonates, achieving selective dimeric macrocycles. These versatile macrocycles exhibit tunable structures and predictable supramolecular assembly, showing potential for molecular recognition and functional materials.

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Area of Science:

  • Organic Chemistry
  • Supramolecular Chemistry
  • Materials Science

Background:

  • Macrocyclic compounds are crucial in molecular recognition and materials science.
  • Synthesizing specific macrocyclic structures, particularly dimeric forms, often presents challenges due to competing oligomerization.

Purpose of the Study:

  • To develop a controlled synthesis for a new class of oxygen-bridged cyclo[2]-malonates.
  • To investigate the structural, conformational, and supramolecular properties of these novel macrocycles.
  • To explore the potential of these macrocycles in molecular recognition, specifically vanadyl ion binding.

Main Methods:

  • Condensation reaction between malonyl dichloride and substituted benzylic α,ω-diols.
  • Optimization of reaction conditions to favor dimeric macrocycle formation.
  • Single-crystal X-ray diffraction for structural and conformational analysis.
  • Investigation of supramolecular assembly through intermolecular interactions (hydrogen bonding, halogen bonding).

Main Results:

  • Successful controlled synthesis of oxygen-bridged cyclo[2]-malonates, selectively yielding dimeric macrocycles.
  • X-ray diffraction confirmed well-defined conformations, tunable cavity sizes, and substituent-dependent stereochemistry.
  • Macrocycles self-assemble into interlocked columnar structures stabilized by hydrogen and halogen bonding.
  • Vanadyl (VO2+) binding is influenced by macrocycle cavity size and preorganization, indicating a structure-function relationship.

Conclusions:

  • Oxygen-bridged cyclo[2]-malonates represent an accessible and versatile macrocyclic platform.
  • These macrocycles offer tunable structural features and predictable supramolecular behavior.
  • The findings suggest significant potential for applications in molecular recognition and the design of functional materials.