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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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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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Radical Substitution: Allylic Bromination01:27

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In organic synthesis, the formation of products can be altered by changing the reaction conditions. For example, a dibromo addition product is formed when propene is treated with bromine at room temperature. In contrast, propene undergoes allylic substitution in non-polar solvents at high temperatures to give 3-bromopropene. In order to avoid the addition reaction, the bromine concentration must be kept as low as possible throughout the reaction. This can be achieved using N-bromosuccinimide...
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In addition to the oxymercuration–demercuration method, which converts the alkenes to alcohols with Markovnikov orientation, a complementary hydroboration-oxidation method yields the anti-Markovnikov product. The hydroboration reaction, discovered in 1959 by H.C. Brown, involves the addition of a B–H bond of borane to an alkene giving an organoborane intermediate. The oxidation of this intermediate with basic hydrogen peroxide forms an alcohol.
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A significant aspect of hydroboration–oxidation is the regio- and stereochemical outcome of the reaction.
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Borane catalyzed polymerization and depolymerization reactions controlled by Lewis acidic strength.

Kori A Andrea1, Mikhailey D Wheeler, Francesca M Kerton

  • 1Department of Chemistry, Memorial University of Newfoundland, 230 Elizabeth Ave, St. John's, NL, A1C 5S7, Canada. fkerton@mun.ca.

Chemical Communications (Cambridge, England)
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Summary
This summary is machine-generated.

Triphenylborane initiates polymerization of anhydrides and epoxides. A more potent borane selectively depolymerizes carbonate blocks, enabling chemical recycling of polymers.

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Area of Science:

  • Polymer Chemistry
  • Organoboron Chemistry

Background:

  • Triphenylborane is a known catalyst for polymerization reactions.
  • The development of catalysts for controlled polymerization and polymer recycling is an active area of research.

Purpose of the Study:

  • To investigate the catalytic activity of triphenylborane in the polymerization of anhydrides and epoxides.
  • To explore the potential of Lewis acidic boranes for selective polymer depolymerization and chemical repurposing.

Main Methods:

  • Catalytic polymerization of anhydrides and epoxides using triphenylborane.
  • Block co-polymerization involving anhydrides/epoxides with epoxides/CO2.
  • Selective depolymerization of carbonate blocks using tris(pentafluorophenyl)borane.

Main Results:

  • Triphenylborane effectively catalyzes the polymerization of anhydrides and epoxides.
  • Block co-polymers were synthesized from anhydride/epoxide and epoxide/CO2 monomers.
  • Tris(pentafluorophenyl)borane selectively depolymerized the carbonate block, yielding cyclic carbonates.

Conclusions:

  • Triphenylborane is a versatile catalyst for epoxide and anhydride polymerization.
  • The selective depolymerization capability of tris(pentafluorophenyl)borane offers a pathway for chemical recycling of the synthesized polymers.