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Olefin Metathesis
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Olefin Metathesis

A special issue of Molecules (ISSN 1420-3049). This special issue belongs to the section "Organic Chemistry".

Deadline for manuscript submissions: closed (30 November 2015) | Viewed by 49585

Special Issue Editor

Prof. Dr. Georgios C. Vougioukalakis

E-Mail Website
Guest Editor
Department of Chemistry, National and Kapodistrian University of Athens, Panepistimiopolis, 15771 Athens, Greece
Interests: organic chemistry; catalysis; organometallic chemistry; materials chemistry; nanostructures; physical organic chemistry
Special Issues, Collections and Topics in MDPI journals

Special Issue Information

Dear Colleagues,

Olefin metathesis is one of the most significant advancements of the last twenty years in the fields of organic chemistry, polymers synthesis, and materials science. It offers a new exciting toolbox of synthetic methods and, therefore, has conditioned the ways chemists design new molecules. Equally important, metathesis has stimulated the preparation of numerous fascinating novel compounds and materials in both industry and academia. The recognition of the great influence of olefin metathesis to the art of chemical synthesis led to the awarding of the 2005 Nobel Prize in Chemistry to Yves Chauvin, Robert H. Grubbs, and Richard R. Schrock.

The goal of the present Special Issue of Molecules is to discuss recent developments in all fields of metathesis. The Special Issue welcomes submissions from all related research areas, including catalyst development, mechanistic and decomposition studies, substrate scope, polymers and materials synthesis, as well as applications in the synthesis of biologically-active compounds and theoretical calculations.

Dr. Georgios C. Vougioukalakis
Guest Editor

Manuscript Submission Information

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Please visit the Instructions for Authors page before submitting a manuscript. The Article Processing Charge (APC) for publication in this open access journal is 2700 CHF (Swiss Francs). Submitted papers should be well formatted and use good English. Authors may use MDPI's English editing service prior to publication or during author revisions.

Keywords

  • catalyst development
  • mechanistic studies
  • olefin metathesis in organic synthesis
  • metathesis polymerizations
  • industrial applications
  • theoretical calculations

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Published Papers (8 papers)

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Editorial

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151 KiB  
Editorial
Recent Advances in Olefin Metathesis
by Georgios C. Vougioukalakis
Molecules 2016, 21(12), 1751; https://doi.org/10.3390/molecules21121751 - 21 Dec 2016
Cited by 2 | Viewed by 4619
Abstract
Olefin metathesis is one of the most significant developments of the last 20 years in the fields of organic chemistry, polymers synthesis, and materials science [1–7]. [...]
Full article
(This article belongs to the Special Issue Olefin Metathesis)

Research

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737 KiB  
Article
Moving from Classical Ru-NHC to Neutral or Charged Rh-NHC Based Catalysts in Olefin Metathesis
by Albert Poater
Molecules 2016, 21(2), 177; https://doi.org/10.3390/molecules21020177 - 30 Jan 2016
Cited by 9 | Viewed by 5091
Abstract
Considering the versatility of oxidation states of rhodium together with the successful background of ruthenium-N-heterocyclic carbene based catalysts in olefin metathesis, it is envisaged the exchange of the ruthenium of the latter catalysts by rhodium, bearing an open-shell neutral rhodium center, [...] Read more.
Considering the versatility of oxidation states of rhodium together with the successful background of ruthenium-N-heterocyclic carbene based catalysts in olefin metathesis, it is envisaged the exchange of the ruthenium of the latter catalysts by rhodium, bearing an open-shell neutral rhodium center, or a +1 charged one. In the framework of in silico experiments, density functional theory (DFT) calculations have been used to plot the first catalytic cycle that as a first step includes the release of the phosphine. DFT is, in this case, the tool that allows the discovery of the less endergonic reaction profile from the precatalytic species for the neutral catalyst with respect to the corresponding ruthenium one; increasing the endergonic character when dealing with the charged system. Full article
(This article belongs to the Special Issue Olefin Metathesis)
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2310 KiB  
Article
Exploring the Reactivity of Na[W2(μ-Cl)3Cl4(THF)2]∙(THF)3 towards the Polymerization of Selected Cycloolefins
by Nikolaos Saragas, Georgios Floros, Grigorios Raptopoulos, Marinos Pitsikalis, Patrina Paraskevopoulou and Konstantinos Mertis
Molecules 2015, 20(12), 21896-21908; https://doi.org/10.3390/molecules201219810 - 8 Dec 2015
Cited by 9 | Viewed by 5121
Abstract
The bimetallic compound Na[W2(μ-Cl)3Cl4(THF)2]·(THF)3 (1, {W 3 W}6+, a′2e′4) is a highly efficient room-temperature initiator for ring opening metathesis polymerization (ROMP) of norbornene (NBE) [...] Read more.
The bimetallic compound Na[W2(μ-Cl)3Cl4(THF)2]·(THF)3 (1, {W 3 W}6+, a′2e′4) is a highly efficient room-temperature initiator for ring opening metathesis polymerization (ROMP) of norbornene (NBE) and some of its derivatives. In most cases, addition of phenylacetylene (PA) as co-initiator improves the catalytic activity and retains the high cis-stereoselectivity. On the other hand, 1 can polymerize cyclopentadiene (CPD), not via a metathetic, but rather, via a cationic mechanism. Here, we present a comparison of the reactivity of the two catalytic systems (1 and 1/PA) between themselves and with other systems reported in the literature, the characterization of the polymers formed and mechanistic aspects of the corresponding reactions. Full article
(This article belongs to the Special Issue Olefin Metathesis)
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1640 KiB  
Article
Olefin Metathesis Reaction in Water and in Air Improved by Supramolecular Additives
by Jasmine Tomasek, Miriam Seßler, Harald Gröger and Jürgen Schatz
Molecules 2015, 20(10), 19130-19141; https://doi.org/10.3390/molecules201019130 - 21 Oct 2015
Cited by 12 | Viewed by 6421
Abstract
A range of water-immiscible commercially available Grubbs-type precatalysts can be used in ring-closing olefin metathesis reaction in high yields. The synthetic transformation is possible in pure water under ambient conditions. Sulfocalixarenes can help to boost the reactivity of the metathesis reaction by [...] Read more.
A range of water-immiscible commercially available Grubbs-type precatalysts can be used in ring-closing olefin metathesis reaction in high yields. The synthetic transformation is possible in pure water under ambient conditions. Sulfocalixarenes can help to boost the reactivity of the metathesis reaction by catalyst activation, improved mass transfer, and solubility of reactants in the aqueous reaction media. Additionally, the use of supramolecular additives allows lower catalyst loadings, but still high activity in pure water under aerobic conditions. Full article
(This article belongs to the Special Issue Olefin Metathesis)
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805 KiB  
Article
Preparation and Reaction Chemistry of Novel Silicon-Substituted 1,3-Dienes
by Partha P. Choudhury and Mark E. Welker
Molecules 2015, 20(9), 16892-16907; https://doi.org/10.3390/molecules200916892 - 16 Sep 2015
Cited by 9 | Viewed by 6260
Abstract
2-Silicon-substituted 1,3-dienes containing non transferrable groups known to promote transmetallation were prepared by Grignard chemistry and enyne metathesis. These dienes participated in one pot metathesis/Diels-Alder reactions in regio- and diastereoselective fashions. Electron-rich alkenes showed the fastest rates in metathesis reactions, and ethylene, a [...] Read more.
2-Silicon-substituted 1,3-dienes containing non transferrable groups known to promote transmetallation were prepared by Grignard chemistry and enyne metathesis. These dienes participated in one pot metathesis/Diels-Alder reactions in regio- and diastereoselective fashions. Electron-rich alkenes showed the fastest rates in metathesis reactions, and ethylene, a commonly used metathesis promoter slowed enyne metathesis. 2-Pyridyldimethylsilyl and 2-thienyldimethylsilyl substituted Diels-Alder cycloadducts participated in cross-coupling chemistry and the 2-thienyldimethylsilyl substituted cycloadducts underwent cross-coupling under very mild reaction conditions. Full article
(This article belongs to the Special Issue Olefin Metathesis)
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841 KiB  
Article
Statistical Ring Opening Metathesis Copolymerization of Norbornene and Cyclopentene by Grubbs’ 1st-Generation Catalyst
by Christiana Nikovia, Andreas-Philippos Maroudas, Panagiotis Goulis, Dionysios Tzimis, Patrina Paraskevopoulou and Marinos Pitsikalis
Molecules 2015, 20(9), 15597-15615; https://doi.org/10.3390/molecules200915597 - 27 Aug 2015
Cited by 10 | Viewed by 5671
Abstract
Statistical copolymers of norbornene (NBE) with cyclopentene (CP) were prepared by ring-opening metathesis polymerization, employing the 1st-generation Grubbs’ catalyst, in the presence or absence of triphenylphosphine, PPh3. The reactivity ratios were estimated using the Finemann-Ross, inverted Finemann-Ross, and Kelen-Tüdos graphical methods, [...] Read more.
Statistical copolymers of norbornene (NBE) with cyclopentene (CP) were prepared by ring-opening metathesis polymerization, employing the 1st-generation Grubbs’ catalyst, in the presence or absence of triphenylphosphine, PPh3. The reactivity ratios were estimated using the Finemann-Ross, inverted Finemann-Ross, and Kelen-Tüdos graphical methods, along with the computer program COPOINT, which evaluates the parameters of binary copolymerizations from comonomer/copolymer composition data by integrating a given copolymerization equation in its differential form. Structural parameters of the copolymers were obtained by calculating the dyad sequence fractions and the mean sequence length, which were derived using the monomer reactivity ratios. The kinetics of thermal decomposition of the copolymers along with the respective homopolymers was studied by thermogravimetric analysis within the framework of the Ozawa-Flynn-Wall and Kissinger methodologies. Finally, the effect of triphenylphosphine on the kinetics of copolymerization, the reactivity ratios, and the kinetics of thermal decomposition were examined. Full article
(This article belongs to the Special Issue Olefin Metathesis)
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Review

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3394 KiB  
Review
ROMP Synthesis of Iron-Containing Organometallic Polymers
by Ileana Dragutan, Valerian Dragutan, Petru Filip, Bogdan C. Simionescu and Albert Demonceau
Molecules 2016, 21(2), 198; https://doi.org/10.3390/molecules21020198 - 6 Feb 2016
Cited by 25 | Viewed by 8259
Abstract
The paper overviews iron-containing polymers prepared by controlled “living” ring-opening metathesis polymerization (ROMP). Developments in the design and synthesis of this class of organometallic polymers are highlighted, pinpointing methodologies and newest trends in advanced applications of hybrid materials based on polymers functionalized with [...] Read more.
The paper overviews iron-containing polymers prepared by controlled “living” ring-opening metathesis polymerization (ROMP). Developments in the design and synthesis of this class of organometallic polymers are highlighted, pinpointing methodologies and newest trends in advanced applications of hybrid materials based on polymers functionalized with iron motifs. Full article
(This article belongs to the Special Issue Olefin Metathesis)
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5973 KiB  
Review
NHC Backbone Configuration in Ruthenium-Catalyzed Olefin Metathesis
by Veronica Paradiso, Chiara Costabile and Fabia Grisi
Molecules 2016, 21(1), 117; https://doi.org/10.3390/molecules21010117 - 20 Jan 2016
Cited by 29 | Viewed by 7176
Abstract
The catalytic properties of olefin metathesis ruthenium complexes bearing N-heterocyclic carbene ligands with stereogenic centers on the backbone are described. Differences in catalytic behavior depending on the backbone configurations of symmetrical and unsymmetrical NHCs are discussed. In addition, an overview on asymmetric [...] Read more.
The catalytic properties of olefin metathesis ruthenium complexes bearing N-heterocyclic carbene ligands with stereogenic centers on the backbone are described. Differences in catalytic behavior depending on the backbone configurations of symmetrical and unsymmetrical NHCs are discussed. In addition, an overview on asymmetric olefin metathesis promoted by chiral catalysts bearing C2-symmetric and C1-symmetric NHCs is provided. Full article
(This article belongs to the Special Issue Olefin Metathesis)
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