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Cycloaddition Reactions: Overview01:16

Cycloaddition Reactions: Overview

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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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Anionic Chain-Growth Polymerization: Mechanism01:04

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The mechanism for anionic chain-growth polymerization involves initiation, propagation, and termination steps. In the initiation step, a nucleophilic anion, such as butyl lithium, initiates the polymerization process by attacking the π bond of the vinylic monomer. As a result, a carbanion, stabilized by the electron‐withdrawing group, is generated. The resulting carbanion acts as a Michael donor in the propagation step and attacks the second vinylic monomer, which acts as a Michael...
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Pericyclic reactions are organic reactions that occur via a concerted mechanism without generating any intermediates. The reactions proceed through the movement of electrons in a closed loop to form a cyclic transition state, where rearrangement of the σ and π bonds yields specific products.
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Cationic Chain-Growth Polymerization: Mechanism00:57

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The cationic polymerization mechanism consists of three steps: initiation, propagation, and termination. In the initiation step of the polymerization process, the π bond of a monomer gets protonated by the Lewis acid catalyst, which is formed from boron trifluoride and water. The protonation of the π bond generates a carbocation stabilized by the electron‐donating group. In the propagation step, the π bond of the second monomer acts as a nucleophile and attacks the...
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Radical Chain-Growth Polymerization: Chain Branching01:17

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The skeletal structure of polymers synthesized via radical polymerization is always branched. For example, the polymerization of ethylene by radical polymerization results in a low-density grade of polyethylene with a heavily branched skeletal structure. Here, the radical site abstracts hydrogen from the growing chain, and the radical site shifts from the end (a primary carbon center) to anywhere within the growing chain (a secondary carbon center). Consequently, the part of the chain from the...
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Radical Chain-Growth Polymerization: Mechanism01:09

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The radical chain-growth polymerization mechanism consists of three steps: initiation, propagation, and termination of polymerization. The polymerization initiates when a free radical generated from the radical initiator adds to the unsaturated bond in the monomer. The unpaired electron of the free radical and one π electron in the unsaturated bond creates a σ bond between the free radical and the monomer. As a result, the other π electron in the unsaturated bond converts this species into...
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Synthesis of Cyclic Polymers and Characterization of Their Diffusive Motion in the Melt State at the Single Molecule Level
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Spontaneous macrocyclization through multiple dynamic cyclic aminal formation.

Daniel Carbajo1, Antonio Jesús Ruiz-Sánchez2, Francisco Nájera2

  • 1Department of Biological Chemistry, Institute of Advanced Chemistry of Catalonia, IQAC-CSIC c/Jordi Girona 18-26, Barcelona, 08034, Spain. ignacio.alfonso@iqac.csic.es.

Chemical Communications (Cambridge, England)
|January 15, 2021
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Summary
This summary is machine-generated.

Tetrakis(aminals) undergo spontaneous [2+2] macrocyclization, offering unexpected stability and modularity. These dynamic covalent systems are water-tolerant and promising for stimulus-responsive materials.

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Area of Science:

  • Dynamic covalent chemistry
  • Supramolecular chemistry
  • Materials science

Background:

  • Aminals are underexplored in dynamic covalent chemistry due to perceived instability.
  • Limited research exists on the macrocyclization of aminal-based systems.

Purpose of the Study:

  • To investigate the potential of aminals in dynamic covalent chemistry.
  • To report the spontaneous macrocyclization of tetrakis(aminals).
  • To evaluate the stability, modularity, and properties of the resulting macrocycles.

Main Methods:

  • Synthesis of tetrakis(aminals).
  • Observation and characterization of spontaneous [2+2] macrocyclization reaction.
  • Analysis of the structural and dynamic properties of the macrocycles.

Main Results:

  • Tetrakis(aminals) spontaneously undergo [2+2] macrocyclization.
  • The resulting macrocycles exhibit unexpected stability.
  • The systems demonstrate structural modularity and water tolerance.

Conclusions:

  • Aminals can be effectively utilized in dynamic covalent chemistry.
  • Tetrakis(aminal) macrocycles are promising building blocks for stimulus-responsive materials.
  • The dynamic nature and stability of these systems open avenues for novel material design.