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Related Concept Videos

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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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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Olefin Metathesis Polymerization: Overview01:13

Olefin Metathesis Polymerization: Overview

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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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Regioselectivity of Electrophilic Additions to Alkenes: Markovnikov's Rule02:17

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If a set of reactants can yield multiple constitutional isomers, but one of the isomers is obtained as the major product, the reaction is said to be regioselective. In such reactions, bond formation or breaking is favored at one reaction site over others.
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Prochirality02:05

Prochirality

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The concept of prochirality leads to the nomenclature of the individual faces of a molecule and plays a crucial role in the enantioselective reaction. It is a concept where two or more achiral molecules react to produce chiral products. A typical process is the reaction of an achiral ketone to generate a chiral alcohol. Here, the achiral reactant reacts with an achiral reducing agent, sodium borohydride, to generate an equimolar mixture of the chiral enantiomers of the product. For example, an...
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Radical Anti-Markovnikov Addition to Alkenes: Overview01:25

Radical Anti-Markovnikov Addition to Alkenes: Overview

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The addition of hydrogen bromide to alkenes in the presence of hydroperoxides or peroxides proceeds via an anti-Markovnikov pathway and yields alkyl bromides.
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Controlled Photoredox Ring-Opening Polymerization of O-Carboxyanhydrides Mediated by Ni/Zn Complexes
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Switchable, chiral aluminium catalysts for ring opening polymerisations.

David T Jenkins1, Elizabeth C Trodden1,2, John M Andresen2

  • 1Institute of Chemical Sciences, Heriot-Watt University, Edinburgh, EH14 4AS, UK. s.mansell@hw.ac.uk.

Dalton Transactions (Cambridge, England : 2003)
|November 11, 2024
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Summary

A new catalytic system enables solvent-free production of polyethers or poly(cyclohexene carbonate) from cyclohexene oxide and carbon dioxide (CO2). This switchable system offers selective synthesis pathways for valuable polymers.

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Area of Science:

  • Polymer Chemistry
  • Catalysis
  • Green Chemistry

Background:

  • Cyclohexene oxide is a versatile monomer for polymer synthesis.
  • Carbon dioxide (CO2) utilization in polymer production is an active area of research for sustainability.
  • Developing efficient and selective catalytic systems for epoxide polymerization is crucial.

Purpose of the Study:

  • To develop a switchable, solvent-free catalytic system for cyclohexene oxide polymerization.
  • To achieve selective synthesis of polyether or poly(cyclohexene carbonate) using the same catalytic system.
  • To explore the use of aluminum-based catalysts in CO2 utilization for polymer synthesis.

Main Methods:

  • Synthesis and characterization of Al methyl aminebis(phenolate) catalysts.
  • Investigation of catalytic activity under CO2 atmosphere for polyether formation.
  • Addition of a bis(triphenylphosphine)iminium chloride (PPNCl) co-catalyst to induce ring-opening copolymerization (ROCoP).
  • Solvent-free reaction conditions were employed.

Main Results:

  • The Al methyl aminebis(phenolate) catalyst selectively initiated polyether formation from cyclohexene oxide under CO2.
  • The addition of PPNCl as a co-catalyst enabled the ring-opening copolymerization (ROCoP) of cyclohexene oxide and CO2.
  • Poly(cyclohexene carbonate) was successfully synthesized via ROCoP.
  • The catalytic system demonstrated switchability between polyether and polycarbonate formation.

Conclusions:

  • A versatile, switchable, and solvent-free catalytic system based on Al methyl aminebis(phenolate) was successfully developed.
  • The system allows for selective synthesis of polyether or poly(cyclohexene carbonate) by controlling the reaction conditions and co-catalyst presence.
  • This approach offers a sustainable route for CO2 utilization in the production of valuable polymers.