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Anionic Chain-Growth Polymerization: Mechanism01:04

Anionic Chain-Growth Polymerization: Mechanism

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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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Anionic Chain-Growth Polymerization: Overview01:20

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The polymerization process that involves carbanion as an intermediate is called anionic polymerization. It is also a type of addition or chain-growth polymerization. Anionic polymerization gets initiated by a strong nucleophile such as an organolithium or a Grignard reagent. The most commonly used initiator for anionic polymerization is butyl lithium. Monomers involved in anionic polymerization must possess a vinyl group bonded to one or two electron-withdrawing groups. For instance,...
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Cationic Chain-Growth Polymerization: Mechanism00:57

Cationic Chain-Growth Polymerization: Mechanism

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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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Reduction of Alkenes: Asymmetric Catalytic Hydrogenation02:17

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Catalytic hydrogenation of alkenes is a transition-metal catalyzed reduction of the double bond using molecular hydrogen to give alkanes. The mode of hydrogen addition follows syn stereochemistry.
The metal catalyst used can be either heterogeneous or homogeneous. When hydrogenation of an alkene generates a chiral center, a pair of enantiomeric products is expected to form. However, an enantiomeric excess of one of the products can be facilitated using an enantioselective reaction or an...
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An allyl group is a three-carbon conjugated system where the sp³-hybridized allylic carbon is bonded to a CH=CH2 group via a single bond. Allyl anions can be obtained by treating propene with a strong base that can deprotonate methyl groups. Allyl cations are formed as intermediates during substitution reactions involving allylic halides. In both cases, the hybridization of the allylic carbon changes from sp3 to sp2, giving rise to a carbon chain with three sp2-hybridized carbons, each with...
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Regioselectivity and Stereochemistry of Acid-Catalyzed Hydration02:34

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The rate of acid-catalyzed hydration of alkenes depends on the alkene's structure, as the presence of alkyl substituents at the double bond can significantly influence the rate.
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Anion-π Catalysis Enabled by the Mechanical Bond.

John R J Maynard1, Bartomeu Galmés2, Athanasios D Stergiou3

  • 1Chemistry, University of Southampton, Highfield, Southampton, S017 1BJ, UK.

Angewandte Chemie (International Ed. in English)
|January 18, 2022
PubMed
Summary
This summary is machine-generated.

We developed novel rotaxane-based catalysts utilizing mechanical bonds for anion-π catalysis. These catalysts selectively promote Michael additions over competing reactions, demonstrating significant catalytic potential.

Keywords:
Anion-π CatalysisDFT CalculationsMechanical BondsRotaxanesSupramolecular Chemistry

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Area of Science:

  • Supramolecular Chemistry
  • Organic Catalysis

Background:

  • Anion-π catalysis utilizes electron-deficient systems to interact with anions.
  • Rotaxanes are mechanically interlocked molecules with unique structural properties.
  • Developing selective catalysts for challenging organic transformations remains a key objective.

Purpose of the Study:

  • To design and synthesize novel rotaxane-based anion-π catalysts.
  • To investigate the role of the mechanical bond in catalytic activity.
  • To achieve high selectivity in organic reactions using these catalysts.

Main Methods:

  • Synthesis of rotaxane architectures featuring bipyridine macrocycles and NDI-containing axles.
  • Catalytic evaluation of rotaxanes in Michael addition reactions.
  • Detailed experimental, electrochemical, and computational analyses to elucidate reaction mechanisms.

Main Results:

  • A series of rotaxane-based anion-π catalysts were successfully synthesized.
  • The mechanical bond within the rotaxanes was found to be crucial for catalytic activity.
  • A [3]rotaxane exhibited >60 fold selectivity for Michael addition over decarboxylation.

Conclusions:

  • Rotaxane-based anion-π catalysts represent a promising new class of catalysts.
  • The mechanical bond plays a critical role in directing catalytic selectivity.
  • These findings open avenues for designing advanced mechanically interlocked catalysts.