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Related Concept Videos

[3,3] Sigmatropic Rearrangement of Allyl Vinyl Ethers: Claisen Rearrangement01:24

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The Claisen rearrangement is a [3,3] sigmatropic rearrangement of allyl vinyl ethers to unsaturated carbonyl compounds. The rearrangement is a concerted pericyclic reaction proceeding via a chair-like transition state.
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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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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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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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Catalysis02:50

Catalysis

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The presence of a catalyst affects the rate of a chemical reaction. A catalyst is a substance that can increase the reaction rate without being consumed during the process. A basic comprehension of a catalysts’ role during chemical reactions can be understood from the concept of reaction mechanisms and energy diagrams.
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Alkynes to Aldehydes and Ketones: Acid-Catalyzed Hydration02:40

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Introduction
Analogous to alkenes, alkynes also undergo acid-catalyzed hydration. While the addition of water to an alkene gives an alcohol, hydration of alkynes produces different products such as aldehydes and ketones.
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Development of Heterogeneous Enantioselective Catalysts using Chiral Metal-Organic Frameworks MOFs
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Mechanochemical Formation, Solution Rearrangements, and Catalytic Behavior of a Polymorphic Ca/K Allyl Complex.

Ross F Koby1, Alicia M Doerr2, Nicholas R Rightmire1

  • 1Department of Chemistry, Vanderbilt University, Nashville, TN 37235, USA.

Chemistry (Weinheim an Der Bergstrasse, Germany)
|April 1, 2021
PubMed
Summary
This summary is machine-generated.

Mechanochemical synthesis produced a novel non-stoichiometric calciate. This compound rearranges rapidly in alkanes and initiates polymerization under mild conditions, showcasing mechanochemistry

Keywords:
Allyl ligandsCalciumMechanochemistryPolymerizationPotassium

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Area of Science:

  • Organometallic Chemistry
  • Materials Science
  • Polymer Chemistry

Background:

  • Mechanochemical synthesis offers unique reaction pathways absent in solution-phase chemistry.
  • Far-from-equilibrium conditions in mechanochemistry can yield high-energy, non-stoichiometric products.
  • Solvent-free reactions are crucial for sustainable chemical synthesis.

Purpose of the Study:

  • To synthesize and characterize novel non-stoichiometric calciate compounds using mechanochemical methods.
  • To investigate the structural rearrangement and reactivity of the synthesized calciate.
  • To explore the potential of the calciate as an initiator for anionic polymerization.

Main Methods:

  • Ball milling of potassium allyl complex (K[A']) and calcium iodide (CaI2).
  • Structural analysis of the resulting calciate using X-ray crystallography.
  • Density Functional Theory (DFT) calculations for structural modeling.
  • Kinetic studies of structural rearrangement in different solvents (arenes and alkanes).
  • Anionic polymerization experiments with methyl methacrylate and isoprene.

Main Results:

  • A non-stoichiometric calciate, K[CaA'3], was synthesized via ball milling.
  • Two distinct structural forms (1 and 2) were identified, differing in allyl ligand coordination (pi/sigma vs. eta3).
  • Structure 1 rearranges to structure 2 rapidly in alkanes and over days in arenes.
  • The calciate complex (2) effectively initiates anionic polymerization of methyl methacrylate and isoprene.
  • Polymerization of isoprene was achieved under exceptionally mild conditions (1 atm, room temperature).

Conclusions:

  • Mechanochemical synthesis provides access to unique non-stoichiometric organometallic compounds.
  • The synthesized calciate exhibits tunable structural dynamics influenced by solvent environment.
  • This calciate represents a highly active initiator for anionic polymerization, particularly for isoprene under mild conditions.
  • The study highlights the potential of mechanochemistry in generating advanced materials and catalysts.