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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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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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Like alkenes, alkynes can be reduced to alkanes in the presence of transition metal catalysts such as Pt, Pd, or Ni. The reaction involves two sequential syn additions of hydrogen via a cis-alkene intermediate.
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Alkenes via Reductive Coupling of Aldehydes or Ketones: McMurry Reaction01:22

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The radical dimerization of ketones or aldehydes gives vicinal diols through a pinacol coupling reaction. However, the behavior of titanium metals used for the reaction as a source of electrons is unusual. When the reaction is carried out in the presence of titanium, diols can be isolated at low temperatures. Else titanium further reacts with diols, forming alkenes through the McMurry reaction.
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Alkenes are converted to 1,2-diols or glycols through a process called dihydroxylation. It involves the addition of two hydroxyl groups across the double bond with two different stereochemical approaches, namely anti and syn. Dihydroxylation using osmium tetroxide progresses with syn stereochemistry.
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Introduction
One of the convenient methods for the preparation of aldehydes and ketones is via hydration of alkynes. Hydroboration-oxidation of alkynes is an indirect hydration reaction in which an alkyne is treated with borane followed by oxidation with alkaline peroxide to form an enol that rapidly converts into an aldehyde or a ketone. Terminal alkynes form aldehydes, whereas internal alkynes give ketones as the final product.
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Improved access to polythioesters by heterobimetallic aluminium catalysis.

Bhargav R Manjunatha1, Merlin R Stühler2, Luise Quick2

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Bimetallic aluminum(III) catalysis significantly enhances thioanhydride/epoxide copolymerization rates and monomer tolerance compared to chromium(III) catalysts. Utilizing sulfurated monomers further boosts reaction efficiency and selectivity.

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Area of Science:

  • Polymer Chemistry
  • Organometallic Catalysis

Background:

  • Copolymerization of thioanhydrides and epoxides is crucial for novel polymer synthesis.
  • Existing chromium(III) catalysts show limitations in rate and monomer tolerance.

Purpose of the Study:

  • To investigate the efficacy of bimetallic aluminum(III) catalysis for thioanhydride/epoxide copolymerization.
  • To compare the performance of Al(III) catalysts with traditional Cr(III) catalysts.
  • To explore the impact of sulfurated monomers on catalytic performance.

Main Methods:

  • Bimetallic Al(III) catalyst synthesis and characterization.
  • Copolymerization reactions using various thioanhydrides and epoxides.
  • Kinetic studies and monomer tolerance assessments.
  • Analysis of product selectivity and polymer properties.

Main Results:

  • Al(III) catalysis demonstrated significantly improved reaction rates over Cr(III) catalysis.
  • Enhanced monomer tolerance was observed with Al(III) catalysts.
  • The use of sulfurated monomers generally led to higher rates and selectivities.
  • Bimetallic Al(III) systems proved effective for controlled copolymerization.

Conclusions:

  • Bimetallic Al(III) catalysts represent a superior alternative to Cr(III) for thioanhydride/epoxide copolymerization.
  • Sulfurated monomers offer advantages in achieving efficient and selective polymerization.
  • This catalytic system opens avenues for developing advanced sulfur-containing polymers.