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Olefin Metathesis Polymerization: Ring-Opening Metathesis Polymerization (ROMP)01:16

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Ring-opening metathesis polymerization or ROMP involves strained cycloalkenes as starting materials. The mechanism of ROMP proceeds by reacting cycloalkene with Grubbs catalyst to give metallacyclobutane intermediate which undergoes a ring-opening reaction to form new carbene. The new carbene reacts with another molecule of cycloalkene. Repetition of these steps leads to the formation of an unsaturated open-chain polymer product. All these steps are reversible, however, relieving the ring...
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Recently, the development of olefin metathesis polymerization advanced the field of polymer synthesis. Simply put, the reorganization of substituents on their double bonds between two olefins in the presence of a catalyst is known as the olefin metathesis reaction. The use of metathesis reaction for polymer synthesis is called olefin metathesis polymerization.
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Due to their highly strained structures, epoxides can readily undergo ring-opening reactions through nucleophilic substitution, either in the presence of an acid or a base. The nucleophilic substitution reactions in the presence of acid are called acid-catalyzed ring-opening reactions, and nucleophilic substitution reactions in the presence of a base are called base-catalyzed ring-opening reactions. Epoxides undergo base-catalyzed ring-opening reactions in the presence of a strong nucleophile...
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Epoxides that are three-membered ring systems are more reactive than other cyclic and acyclic ethers. The high reactivity of epoxides originates from the strain present in the ring. This ring strain acts as a driving force for epoxides to undergo ring-opening reactions either with halogen acids or weak nucleophiles in the presence of mild acid. The acid catalyst converts the epoxide oxygen, a poor leaving group, into an oxonium ion, a better leaving group, making the reaction feasible. The...
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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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Acyclic diene metathesis polymerization or ADMET polymerization involves cross-metathesis of terminal dienes, such as 1,8-nonadiene, to give linear unsaturated polymer and ethylene. As ADMET is a reversible process, the formed ethylene gas must be removed from the reaction mixture to complete the polymerization process.
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Poly(thioester) by Organocatalytic Ring-Opening Polymerization.

Timothy J Bannin1, Matthew K Kiesewetter1

  • 1Department of Chemistry, University of Rhode Island, Kingston, Rhode Island 02881, United States.

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|May 17, 2016
PubMed
Summary
This summary is machine-generated.

Organocatalysts enable ring-opening polymerization of thiolactone monomers. Thiourea catalysts effectively polymerize ε-thiocaprolactone, yielding poly(thiocaprolactone) with controlled properties.

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Area of Science:

  • Polymer Chemistry
  • Organic Chemistry
  • Materials Science

Background:

  • Organocatalysts are widely used for cyclic ester polymerization.
  • Thiolactones, sulfur analogs of lactones, present unique polymerization challenges.
  • Understanding polymerization mechanisms is key to controlling polymer properties.

Purpose of the Study:

  • To investigate the ring-opening polymerization (ROP) of ε-thiocaprolactone (tCL) using organocatalysts.
  • To explore the mechanism of tCL polymerization, including the role of H-bonding.
  • To compare the polymerization of tCL with that of ε-caprolactone.

Main Methods:

  • Application of organocatalysts, typically used for cyclic esters, to the thiolactone tCL.
  • Investigation of polymerization mechanisms in the presence and absence of H-bond donors.
  • Characterization of the resulting poly(thiocaprolactone) using techniques like GPC to determine molecular weight and dispersity.

Main Results:

  • Organocatalysts are effective for tCL ring-opening polymerization.
  • A nucleophilic polymerization mechanism is proposed in the absence of H-bond donors.
  • H-bonding organocatalysts, specifically thiourea with a base, are also effective.
  • Poly(thiocaprolactone) exhibited higher dispersity than poly(caprolactone) due to increased thiol nucleophilicity, but transesterification was suppressed by thiourea.
  • tCL shows thermodynamic similarity to ε-caprolactam and kinetic similarity to ε-caprolactone.

Conclusions:

  • Organocatalysis is a viable strategy for synthesizing poly(thiocaprolactone).
  • Thiourea catalysts offer control over polymerization, suppressing side reactions.
  • The study provides insights into the polymerization behavior of thiolactones, distinct from lactones.