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Journal articles on the topic 'Metathesis'

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Author: Grafiati

Published: 4 June 2021

Last updated: 25 May 2024

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1

Schindler, Corinna, and Jacob Ludwig. "Lewis Acid Catalyzed Carbonyl–Olefin Metathesis." Synlett 28, no. 13 (May 16, 2017): 1501–9. http://dx.doi.org/10.1055/s-0036-1588827.

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Olefin–olefin metathesis has led to important advances in diverse fields of research, including synthetic chemistry, materials science, and chemical biology. The corresponding carbonyl–olefin metathesis also enables direct carbon–carbon bond formation from readily available precursors, however, currently available synthetic procedures are significantly less advanced. This Synpacts article provides an overview of recent achievements in the field of Lewis acid mediated and Lewis acid catalyzed carbonyl–olefin metathesis reactions.1 Lewis Acid Mediated Carbonyl–Olefin Metathesis2 Lewis Acid Catalyzed Carbonyl–Olefin Metathesis

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2

Dragutan, V., I. Dragutan, and A. T. Balaban. "Single-Site Ruthenium Metathesis Catalysts." Platinum Metals Review 45, no. 4 (October 1, 2001): 155–63. http://dx.doi.org/10.1595/003214001x454155163.

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This paper presents an up-to-date investigation relating to the design and synthesis of the recently disclosed single-site ruthenium carbene metathesis catalysts. Created as a convenient counterpart of the earlier tungsten and molybdenum carbene catalysts, these novel ruthenium carbene complexes bear specific heterocyclic ligands and display comparable activity and selectivity in metathesis reactions, as well as good tolerance toward organic functionalities, air and moisture. Due to their unique properties, they can be successfully applied in numerous organic and polymer syntheses involving cross-metathesis, ring-opening and ring-closing metatheses, as well as ring-opening metathesis polymerisation. This paper updates our previous review on metathesis reactions published in this Journal last year.

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3

Sabatino, Valerio, and Thomas R. Ward. "Aqueous olefin metathesis: recent developments and applications." Beilstein Journal of Organic Chemistry 15 (February 14, 2019): 445–68. http://dx.doi.org/10.3762/bjoc.15.39.

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Olefin metathesis is one of the most powerful C–C double-bond-forming reactions. Metathesis reactions have had a tremendous impact in organic synthesis, enabling a variety of applications in polymer chemistry, drug discovery and chemical biology. Although challenging, the possibility to perform aqueous metatheses has become an attractive alternative, not only because water is a more sustainable medium, but also to exploit biocompatible conditions. This review focuses on the progress made in aqueous olefin metatheses and their applications in chemical biology.

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4

Lambert, Tristan H. "Development of a Hydrazine-Catalyzed Carbonyl-Olefin Metathesis Reaction." Synlett 30, no. 17 (June 5, 2019): 1954–65. http://dx.doi.org/10.1055/s-0039-1689924.

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Carbonyl-olefin metathesis is a potentially powerful yet underexplored reaction in organic synthesis. In recent years, however, this situation has begun to change, most notably with the introduction of several different catalytic technologies. The development of one of those new strategies, based on hydrazine catalysts and a novel [3+2] paradigm for double bond metathesis, is discussed herein. First, the stage is set with a description of some potential applications of carbonyl-olefin metathesis and a discussion of alternative strategies for this intriguing reaction.1 Introduction2 Potential Applications of Carbonyl-Olefin Metathesis3 Carbonyl-Olefin Metathesis Strategies4 Direct (Type I): Non-Catalytic5 Direct (Type I): Acid-Catalyzed6 Indirect (Type II): Metal Alkylidenes7 Indirect (Type III): Hydrazine-Catalyzed8 Conclusion

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5

Groso, Emilia, and Corinna Schindler. "Recent Advances in the Application of Ring-Closing Metathesis for the Synthesis of Unsaturated Nitrogen Heterocycles." Synthesis 51, no. 05 (February 8, 2019): 1100–1114. http://dx.doi.org/10.1055/s-0037-1611651.

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This short review summarizes recent advances relating to the application of ring-closing olefin-olefin and carbonyl-olefin metathesis reactions towards the synthesis of unsaturated five- and six-membered nitrogen heterocycles. These developments include catalyst modifications and reaction designs that will enable access to more complex nitrogen heterocycles.1 Introduction2 Expansion of Ring-Closing Metathesis Methods3 Evaluation of Catalyst Design4 Indenylidene Catalysts5 Unsymmetrical N-Heterocyclic Carbene Ligands6 Carbonyl-Olefin Metathesis7 Conclusions

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6

Rogalski, Szymon, and Cezary Pietraszuk. "Application of Olefin Metathesis in the Synthesis of Carbo- and Heteroaromatic Compounds—Recent Advances." Molecules 28, no. 4 (February 9, 2023): 1680. http://dx.doi.org/10.3390/molecules28041680.

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The olefin metathesis reaction has found numerous applications in organic synthesis. This is due to a number of advantages, such as the tolerance of most functional groups and sterically demanding olefins. This article reviews recent advances in the application of the metathesis reaction, particularly the metathetic cyclization of dienes and enynes, in synthesis protocols leading to (hetero)aromatic compounds.

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7

Sauer, D. F., S. Gotzen, and J. Okuda. "Metatheases: artificial metalloproteins for olefin metathesis." Organic & Biomolecular Chemistry 14, no. 39 (2016): 9174–83. http://dx.doi.org/10.1039/c6ob01475e.

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8

Kiss, Loránd, Márton Kardos, Csaba Vass, and Ferenc Fülöp. "Application of Metathesis Reactions in the Synthesis and Transformations of Functionalized β-Amino Acid Derivatives." Synthesis 50, no. 18 (July 26, 2018): 3571–88. http://dx.doi.org/10.1055/s-0036-1591600.

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Because of their biological relevance, cyclic β-amino acids have generated increasing interest and had significant impact in drug research over the past two decades. Their preparation and further functionalization towards new types of molecular entities have received large interest in synthetic and medicinal chemistry. Various types of metathesis reactions, such as ring-opening (ROM), ring-closing (RCM), or cross metathesis (CM) are used widely for access to either alicyclic β-amino acids or other densely functionalized derivatives of this group of compounds. This account intends to provide an insight into the most relevant synthetic routes to this class of derivatives with the application of metathesis reactions. The review focuses on the presentation of selective and stereocontrolled methodologies in view of versatility, robustness, limitations and efficiency.1 Introduction2 Synthesis and Transformation of Cyclic β-Amino Acids through Metathesis Reactions2.1 Synthesis of Five- and Six-Membered Cyclic β-Amino Acids by Ring-Closing Metathesis2.2 Synthesis of Five- and Six-Membered Cyclic β-Amino Acids by Cross Metathesis2.3 Synthesis of β-Amino Acids with Larger Ring Systems by Ring- Closing Metathesis2.4 Synthesis of β-Amino Acids with Condensed Ring Systems by Ring-Rearrangement Metathesis2.5 Stereocontrolled One-Step Synthesis of Functionalized Cispentacin and Transpentacin Derivatives2.5.1 Stereocontrolled Synthesis of Functionalized Cispentacin and Transpentacin Derivatives through Ring-Opening Metathesis of Norbornene β-Amino Acid Derivatives2.5.2 Stereocontrolled Synthesis of Functionalized Azetidinones and β-Amino Acid Derivatives from Condensed Ring β-Lactams by Ring-Opening Metathesis2.5.3 Carbon–Carbon Double Bond Functionalization of β-Amino Acid Derivatives and β-Lactams with α,β-Unsaturated Carbonyl Compounds through Cross Metathesis2.5.4 Synthesis of Functionalized β-Amino Acid Derivatives and β-Lactams through Chemoselective Cross Metathesis3 Conclusions and Outlook

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9

Kotha, Sambasivarao, Shilpi Misra, Gaddamedi Sreevani, and Bandarugattu Babu. "Non-Metathetic Behaviour of Olefin Metathesis Catalysts." Current Organic Chemistry 17, no. 22 (October 1, 2013): 2776–95. http://dx.doi.org/10.2174/13852728113179990118.

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10

Sarabia, Francisco, and Iván Cheng-Sánchez. "Recent Advances in Total Synthesis via Metathesis Reactions." Synthesis 50, no. 19 (July 18, 2018): 3749–86. http://dx.doi.org/10.1055/s-0037-1610206.

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The metathesis reactions, in their various versions, have become a powerful and extremely valuable tool for the formation of carbon–carbon bonds in organic synthesis. The plethora of available catalysts to perform these reactions, combined with the various transformations that can be accomplished, have positioned the metathesis processes as one of the most important reactions of this century. In this review, we highlight the most relevant synthetic contributions published between 2012 and early 2018 in the field of total synthesis, reflecting the state of the art of this chemistry and demonstrating the significant synthetic potential of these methodologies.1 Introduction2 Alkene Metathesis in Total Synthesis2.1 Total Synthesis Based on a Ring-Closing-Metathesis Reaction2.2 Total Synthesis Based on a Cross-Metathesis Reaction2.3 Strategies for Selective and Efficient Metathesis Reactions of Alkenes2.3.1 Temporary Tethered Ring-Closing Metathesis2.3.2 Relay Ring-Closing Metathesis2.3.3 Stereoselective Alkene Metathesis2.3.4 Alkene Metathesis in Tandem Reactions3 Enyne Metathesis in Total Synthesis3.1 Total Syntheses Based on a Ring-Closing Enyne-Metathesis Reaction3.2 Total Syntheses Based on an Enyne Cross-Metathesis Reaction3.3 Enyne Metathesis in Tandem Reactions4 Alkyne Metathesis in Total Synthesis4.1 Total Synthesis Based on a Ring-Closing Alkyne-Metathesis Reaction4.2 Other Types of Alkyne-Metathesis Reactions5 Conclusions

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11

Bruneau, Christian, Cédric Fischmeister, Dalmo Mandelli, Wagner A. Carvalho, Eduardo N. dos Santos, Pierre H. Dixneuf, and Luciana Sarmento Fernandes. "Transformations of terpenes and terpenoids via carbon–carbon double bond metathesis." Catalysis Science & Technology 8, no. 16 (2018): 3989–4004. http://dx.doi.org/10.1039/c8cy01152d.

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The review reports on transformations of unsaturated terpenes and terpenoids via olefin metathesis processes including ring closing metathesis of dienes, cross metathesis with functional olefins and ethenolysis, and ring opening metathesis as well as ring opening/cross metathesis.

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12

Khafidhoh, Khafidhoh. "A Child’s Language Acquisition: The Metathesis Phenomena." Metathesis: Journal of English Language, Literature, and Teaching 3, no. 1 (April 30, 2019): 1. http://dx.doi.org/10.31002/metathesis.v3i1.1141.

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Metathesis is one of the unique phenomena among the children during their language acquisition phase. This research aims at investigating the metathesis phenomena happens in a child. The research method used in this research is qualitative method, especially case study. The results of this research show that the metathesis phenomena happen in that child is related to 16 phonemes. It includes pure metathesis in the same syllable phonemes, pure metathesis in the different syllables phonemes, metathesis followed by phonemes addition, metathesis followed by phonemes omission, and metathesis followed by both of them. The findings from this research will be the basis in conducting the following relevant studies.

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13

Saputri, Nurul Intan, Albiansyah Albiansyah, and Fahriany Fahriany. "THE PHONOLOGICAL PROCESSES OF METATHESIS WORDS IN A CHILDS’ LANGUAGE ACQUISITION: A CASE STUDY OF A 3-YEAR-OLD CHILD." Lexeme : Journal of Linguistics and Applied Linguistics 3, no. 1 (January 5, 2021): 1. http://dx.doi.org/10.32493/ljlal.v3i1.8565.

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AbstractMetathesis is one of the unique phenomena among the children during their language acquisition phase. The aim of this study was to examine the phonological process of phenomena metathesis words that happen in a child’s language acquisition especially children with aged three half years. The participant of this research was a 3.5-year-old child. She is researcher’s daughter. The research method used in this research is qualitative method with a case study design was employed in this study. The data were collected through observation, documentation, and daily notes or diary. The results of this research showed that the metathesis phenomena happen in that child was related to ten phonemes. It included pure metathesis in the same syllable phonemes, pure metathesis in the different syllable’s phonemes, metathesis followed by phonemes addition, and metathesis followed by phonemes omission. The study revealed some words containing metathesis that produced by the participant. Six pure metathesis words in the same syllable and six pure metathesis words in the different syllables then followed by addition phonemes involves in two words Keywords: Child, Language Acquisition, Metathesis, Phonemes, Phonological

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14

Roscales, Silvia, and Joaquín Plumet. "Ring Rearrangement Metathesis in 7-Oxabicyclo[2.2.1]heptene (7-Oxanorbornene) Derivatives. Some Applications in Natural Product Chemistry." Natural Product Communications 12, no. 5 (May 2017): 1934578X1701200. http://dx.doi.org/10.1177/1934578x1701200517.

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Metathesis reactions is firmly established as a valuable synthetic tool in organic chemistry, clearly comparable with the venerable Diels-Alder and Wittig reactions and, more recently, with the metal-catalyzed cross-coupling reactions. Metathesis reactions can be considered as a fascinating synthetic methodology, allowing different variants regarding substrate (alkene and alkyne metathesis) and type of metathetical reactions. On the other hand, tandem metathesis reactions such Ring Rearrangement Metathesis (RRM) and the coupling of metathesis reaction with other reactions of alkenes such as Diels-Alder or Heck reactions, makes metathesis one of the most powerful and reliable synthetic procedure. In particular, Ring-Rearrangement Metathesis (RRM) refers to the combination of several metathesis transformations into a domino process such as ring-opening metathesis (ROM)/ring-closing metathesis (RCM) and ROM-cross metathesis (CM) in a one-pot operation. RRM delivers complex frameworks that are difficult to assemble by conventional methods constitutingan atom economic process. RRM is applicable to mono- and polycyclic systems of varying ring sizes such as cyclopropene, cyclobutene, cyclopentene, cyclohexene, pyran systems, bicyclo[2.2.1]heptene derivatives, bicyclo[2.2.2]octene derivatives, bicyclo[3.2.1]octene derivatives and bicyclo[3.2.1]octene derivatives. In this review our attention has focused on the RRM reactions in 7-oxabicyclo[2.2.1]heptene derivatives and on their application in the synthesis of natural products or significant subunits of them.

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15

Fogg, Deryn E. "Inside the black box — Perspectives on transformations in catalysis." Canadian Journal of Chemistry 86, no. 10 (October 1, 2008): 931–41. http://dx.doi.org/10.1139/v08-103.

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Tandem catalysis and olefin metathesis are powerful tools in the development of sustainable synthetic practices. This Award Lecture describes our advances in designing new tandem metathesis-hydrogenation methodologies for the synthesis of “designer materials” and Ru-pseudohalide metathesis catalysts that amplify opportunities for tuning catalyst activity, selectivity, and lifetime. Also discussed is the operation of a previously unrecognized oligomerization-backbiting pathway in ring-closing metathesis of conformationally flexible α,ω-dienes, which has important implications for the sustainable synthesis of medium and large rings.Key words: tandem catalysis, green chemistry, olefin metathesis, ring-closing metathesis, mechanism.

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16

Michaudel, Quentin, Samuel J. Kempel, and Ting-Wei Hsu. "Stereoretentive Olefin Metathesis: A New Avenue for the Synthesis of All-cis Poly(p-phenylene vinylene)s and Stereodefined Polyalkenamers." Synlett 32, no. 09 (January 12, 2021): 851–57. http://dx.doi.org/10.1055/a-1352-1605.

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AbstractOlefin metathesis has tremendously impacted all fields of synthetic chemistry. However, the control of the olefin stereochemistry during this process remains a grand challenge. Recent innovations in catalyst design have permitted control of the stereochemistry of the olefin product. Here, we discuss the development of stereoretentive olefin metathesis, with an emphasis on the synthesis of stereodefined polyalkenamers through ring-opening metathesis polymerization (ROMP). We then present our application of this unique reaction manifold to the preparation of all-cis poly(p-phenylene vinylene)s (PPVs). A dithiolate Ru catalyst was found to deliver perfect cis selectivity for the polymerization of a paracyclophane diene monomer. By using optimized conditions, all-cis PPVs with narrow dispersities and predictable molar masses were obtained by varying the ratio of monomer to catalyst. The high chain fidelity of the stereoretentive ROMP with a paracyclophane diene monomer enabled the preparation of well-defined diblock copolymers with a norbornene co-monomer. Photochemical isomerization of all-cis to all-trans PPVs was effected with both homopolymers and diblock copolymers. This process was shown to be selective for the PPV block, and resulted in changes in optical properties, polymer size, and solubility. Stereoretentive ROMP provides a promising platform for synthesizing polymers with unique properties, including photoresponsive all-cis PPVs with living characteristics.1 Introduction2 Synthetic Applications of Stereoretentive Olefin Metathesis3 Stereocontrol of Polyalkenamers through Stereoretentive ROMP4 Stereoretentive ROMP To Access All-cis Poly(p-phenylene vinylene)s5 Conclusion

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17

Das, Aniruddha, Soumen Sarkar, Baitan Chakraborty, Abhishek Kar, and Umasish Jana. "Catalytic Alkyne/Alkene-Carbonyl Metathesis: Towards the Development of Green Organic Synthesis." Current Green Chemistry 7, no. 1 (May 15, 2020): 5–39. http://dx.doi.org/10.2174/2213346106666191105144019.

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The construction of carbon-carbon bond through the metathesis reactions between carbonyls and olefins or alkynes has attracted significant interest in organic chemistry due to its high atomeconomy and efficiency. In this regard, carbonyl–alkyne metathesis is well developed and widely used in organic synthesis for the atom-efficient construction of various carbocycles and heterocycles in the presence of catalytic Lewis acids or Brønsted acids. On the other hand, alkene-carbonyl metathesis is recently developed and has been a topic of great importance in the field of organic chemistry because they possess attractive qualities involving metal-mediated, metal-free intramolecular, photochemical, Lewis acid-mediated ring-closing metathesis, ring-opening metathesis and cross-metathesis. This review covers most of the strategies of carbonyl–alkyne and carbonyl–olefin metathesis reactions in the synthesis of complex molecules, natural products and pharmaceuticals as well as provides an overview of exploration of the metathesis reactions with high atom-economy as well as environmentally and ecologically benign reaction conditions.

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18

Patrzałek, Michał, Aleksandra Zasada, Anna Kajetanowicz, and Karol Grela. "Tandem Olefin Metathesis/α-Ketohydroxylation Revisited." Catalysts 11, no. 6 (June 9, 2021): 719. http://dx.doi.org/10.3390/catal11060719.

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EWG-activated and polar quaternary ammonium salt-tagged ruthenium metathesis catalysts have been applied in a two-step one-pot metathesis-oxidation process leading to functionalized α-hydroxyketones (acyloins). In this assisted tandem process, the metathesis catalyst is used first to promote ring-closing metathesis (RCM) and cross-metathesis (CM) steps, then upon the action of Oxone™ converts into an oxidation catalyst able to transform the newly formed olefinic product into acyloin under mild conditions.

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19

Ehrhorn, Henrike, Janin Schlösser, Dirk Bockfeld, and Matthias Tamm. "Efficient catalytic alkyne metathesis with a fluoroalkoxy-supported ditungsten(III) complex." Beilstein Journal of Organic Chemistry 14 (September 18, 2018): 2425–34. http://dx.doi.org/10.3762/bjoc.14.220.

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The molybdenum and tungsten complexes M2(OR)6 (Mo2F6, M = Mo, R = C(CF3)2Me; W2F3, M = W, R = OC(CF3)Me2) were synthesized as bimetallic congeners of the highly active alkyne metathesis catalysts [MesC≡M{OC(CF3) n Me3− n }] (MoF6, M = Mo, n = 2; WF3, M = W, n = 1; Mes = 2,4,6-trimethylphenyl). The corresponding benzylidyne complex [PhC≡W{OC(CF3)Me2}] (W Ph F3) was prepared by cleaving the W≡W bond in W2F3 with 1-phenyl-1-propyne. The catalytic alkyne metathesis activity of these metal complexes was determined in the self-metathesis, ring-closing alkyne metathesis and cross-metathesis of internal and terminal alkynes, revealing an almost equally high metathesis activity for the bimetallic tungsten complex W2F3 and the alkylidyne complex W Ph F3. In contrast, Mo2F6 displayed no significant activity in alkyne metathesis.

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20

Takahashi, Chikako. "No transposition in Harmonic Serialism." Phonology 36, no. 4 (November 2019): 695–726. http://dx.doi.org/10.1017/s0952675719000344.

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This paper presents a Harmonic Serialism analysis of synchronic metathesis, and proposes to eliminate transposition as an atomic operation, instead analysing metathesis as a result of the sequential application of simpler operations. The analysis of phase alternations in Rotuman offers a unified account of metathesis, deletion and umlaut as all undergoing splitting followed by fusion. A non-transposition analysis of multiple metathesis in Kwara'ae shows that a prosodically motivated locality restriction on the splitting domain is crucial in deriving the attested patterns. CC metathesis in Balangao is analysed as fusion followed by splitting. Eliminating transposition has several benefits: (a) it simplifies the inventory of operations in Harmonic Serialism, (b) it correctly predicts the locality restrictions on metathesis patterns with smaller constraint sets and (c) it accounts for the differences observed in the segment types involved in CV(VC) vs. CC metathesis.

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21

Dragutan, V., I. Dragutan, and A. T. Balaban. "Metathesis Catalysed by the Platinum Group Metals." Platinum Metals Review 44, no. 2 (April 1, 2000): 58–66. http://dx.doi.org/10.1595/003214000x4425866.

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Metathesis (from the Greek meta tithemi = change place) describes in chemistry the interchange of atoms between two molecules. The metathesis of olefins is the formal scission of a pair of double bonds, followed by the interchange of their carbon atoms. Metathesis polymerisation of cycloolefins refers to the apparent ring cleavage at the double bond, accompanied by polymerisation to unsaturated polymers (la, lb). Nowadays metathesis is established as a powerful method of synthesis in organic and polymer chemistry (), and platinum group metal catalysts have played a prominent role in this achievement. Metathesis has resulted in both unique syntheses and novel compounds. In this review metathesis reactions catalysed by platinum group metals are described, specifically the types of catalyst, their metathesis activity and various ring-opening and ring-closing reactions. Part II of this paper will be published in the July issue of this Journal.

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22

Astruc, Didier, Abdou K. Diallo, Sylvain Gatard, Liyuan Liang, Cátia Ornelas, Victor Martinez, Denise Méry, and Jaime Ruiz. "Olefin metathesis in nano-sized systems." Beilstein Journal of Organic Chemistry 7 (January 19, 2011): 94–103. http://dx.doi.org/10.3762/bjoc.7.13.

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The interplay between olefin metathesis and dendrimers and other nano systems is addressed in this mini review mostly based on the authors’ own contributions over the last decade. Two subjects are presented and discussed: (i) The catalysis of olefin metathesis by dendritic nano-catalysts via either covalent attachment (ROMP) or, more usefully, dendrimer encapsulation – ring closing metathesis (RCM), cross metathesis (CM), enyne metathesis reactions (EYM) – for reactions in water without a co-solvent and (ii) construction and functionalization of dendrimers by CM reactions.

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23

Chalker, Justin M. "Allyl Sulfides: Reactive Substrates for Olefin Metathesis." Australian Journal of Chemistry 68, no. 12 (2015): 1801. http://dx.doi.org/10.1071/ch15311.

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Allyl sulfides have gained traction in recent years as promoters for olefin metathesis. The high reactivity of allyl sulfides in olefin metathesis is remarkable, given that many sulfur-containing substrates are incompatible with ruthenium-based olefin metathesis catalysts. In stark contrast, allyl sulfides actually enhance the rate of metathesis in comparison with other alkenes, when matched with a suitable catalyst. This review examines how the high reactivity of allyl sulfides in olefin metathesis has been harnessed in diverse areas of synthesis. In the cases examined, allyl sulfides have been explicitly incorporated into substrates to promote olefin metathesis. Recent insights into catalyst considerations, applications in chemical and biochemical synthesis, and future opportunities are discussed.

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24

Wappel, Julia, César A. Urbina-Blanco, Mudassar Abbas, Jörg H. Albering, Robert Saf, Steven P. Nolan, and Christian Slugovc. "Halide exchanged Hoveyda-type complexes in olefin metathesis." Beilstein Journal of Organic Chemistry 6 (November 23, 2010): 1091–98. http://dx.doi.org/10.3762/bjoc.6.125.

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The aims of this contribution are to present a straightforward synthesis of 2nd generation Hoveyda-type olefin metathesis catalysts bearing bromo and iodo ligands, and to disclose the subtle influence of the different anionic co-ligands on the catalytic performance of the complexes in ring opening metathesis polymerisation, ring closing metathesis, enyne cycloisomerisation and cross metathesis reactions.

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25

Krehl, Stefan, Diana Geißler, Sylvia Hauke, Oliver Kunz, Lucia Staude, and Bernd Schmidt. "The catalytic performance of Ru–NHC alkylidene complexes: PCy3 versus pyridine as the dissociating ligand." Beilstein Journal of Organic Chemistry 6 (December 15, 2010): 1188–98. http://dx.doi.org/10.3762/bjoc.6.136.

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The catalytic performance of NHC-ligated Ru-indenylidene or benzylidene complexes bearing a tricyclohexylphosphine or a pyridine ligand in ring closing metathesis (RCM), cross metathesis, and ring closing enyne metathesis (RCEYM) reactions is compared. While the PCy3 complexes perform significantly better in RCM and RCEYM reactions than the pyridine complex, all catalysts show similar activity in cross metathesis reactions.

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26

Schmidt, Bernd. "Connecting catalytic cycles by organometallic transformations in situ: Novel perspectives in the olefin metathesis field." Pure and Applied Chemistry 78, no. 2 (January 1, 2006): 469–76. http://dx.doi.org/10.1351/pac200678020469.

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Tandem sequences consisting of an olefin metathesis step and a subsequent non-metathesis reaction become accessible by organometallic transformations of the Ru-carbene species in situ. This contribution highlights some tandem sequences that rely on the conversion of the metathesis catalyst to Ru-hydrides, with special emphasis on the tandem ring-closing metathesis (RCM)-double-bond isomerization sequence.

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27

Kalimi, Isaac. "Literary-Stylistic Metathesis in the Hebrew Bible." Vetus Testamentum 70, no. 4-5 (January 21, 2020): 603–19. http://dx.doi.org/10.1163/15685330-00001401.

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Abstract Biblical scholarship has concentrated almost exclusively on cases of unintentional metathesis, particularly as a tool of textual criticism. But metathesis is not only a result of accidents and mistakes; it can also be deliberately employed as a literary-stylistic device. Accordingly, this study addresses all three of these categories of metathesis in the biblical literature, but focuses particularly on Literary-stylistic metathesis that is an intentional form of metathesis, in which an author or editor has deliberately chosen to use two or more words that share the same characters in inverse order.

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28

Lin, Yuya A., and Benjamin G. Davis. "The allylic chalcogen effect in olefin metathesis." Beilstein Journal of Organic Chemistry 6 (December 23, 2010): 1219–28. http://dx.doi.org/10.3762/bjoc.6.140.

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Olefin metathesis has emerged as a powerful tool in organic synthesis. The activating effect of an allylic hydroxy group in metathesis has been known for more than 10 years, and many organic chemists have taken advantage of this positive influence for efficient synthesis of natural products. Recently, the discovery of the rate enhancement by allyl sulfides in aqueous cross-metathesis has allowed the first examples of such a reaction on proteins. This led to a new benchmark in substrate complexity for cross-metathesis and expanded the potential of olefin metathesis for other applications in chemical biology. The enhanced reactivity of allyl sulfide, along with earlier reports of a similar effect by allylic hydroxy groups, suggests that allyl chalcogens generally play an important role in modulating the rate of olefin metathesis. In this review, we discuss the effect of allylic chalcogens in olefin metathesis and highlight its most recent applications in synthetic chemistry and protein modifications.

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29

Vosloo, H. C. M., and J. A. K. Du Plessis. "Die metatese van alkyne." Suid-Afrikaanse Tydskrif vir Natuurwetenskap en Tegnologie 10, no. 2 (July 8, 1991): 72–79. http://dx.doi.org/10.4102/satnt.v10i2.490.

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The alkyne metathesis reaction is a direct result of the known and intensively studied alkene or olefin metathesis reaction. Unfortunately this reaction was never studied as intensively as the alkene metathesis reaction, mainly because of a lack of active catalytic systems. In the alkyn metathesis reaction the carbon-carbon triple bonds are broken and rearranged to give a redistribution of alkylidyne groups.

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30

Kotha, Sambasivarao, Milind Meshram, Priti Khedkar, Shaibal Banerjee, and Deepak Deodhar. "Recent applications of ring-rearrangement metathesis in organic synthesis." Beilstein Journal of Organic Chemistry 11 (October 7, 2015): 1833–64. http://dx.doi.org/10.3762/bjoc.11.199.

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Ring-rearrangement metathesis (RRM) involves multiple metathesis processes such as ring-opening metathesis (ROM)/ring-closing metathesis (RCM) in a one-pot operation to generate complex targets. RRM delivers complex frameworks that are difficult to assemble by conventional methods. The noteworthy point about this type of protocol is multi-bond formation and it is an atom economic process. In this review, we have covered literature that appeared during the last seven years (2008–2014).

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31

Smulik, Jason A., and Steven T. Diver. "Tandem dienyne cross-metathesis/ring-closing metathesis." Tetrahedron Letters 42, no. 2 (January 2001): 171–74. http://dx.doi.org/10.1016/s0040-4039(00)01922-5.

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32

Kotha, Sambasivarao, Shilpi Misra, Gaddamedi Sreevani, and Bandarugattu V. Babu. "ChemInform Abstract: Non-Metathetic Behaviour of Olefin Metathesis Catalysts." ChemInform 46, no. 4 (January 2015): no. http://dx.doi.org/10.1002/chin.201504259.

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33

Miętkiewski, Miłosz, Beata Powała, Bartosz Staniszewski, Maciej Kubicki, Włodzimierz Urbaniak, and Cezary Pietraszuk. "Metathesis transformations of unsaturated derivatives of β-diketones." Open Chemistry 9, no. 4 (August 1, 2011): 728–36. http://dx.doi.org/10.2478/s11532-011-0055-1.

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AbstractSelected β-diketones bearing unsaturated derivatives have been demonstrated to undergo homo-metathesis and cross-metathesis with selected olefins in the presence of Grubbs catalysts. The reactions led to respective homo- and cross-metathesis products mainly with good yields and selectivities.

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34

Sánchez-Roselló, María, Carlos del Pozo, and Javier Miró. "Cross-Metathesis/Intramolecular (Hetero-)Michael Addition: A Convenient Sequence for the Generation of Carbo- and Heterocycles." Synthesis 49, no. 13 (May 4, 2017): 2787–802. http://dx.doi.org/10.1055/s-0036-1589497.

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The high stability and functional group compatibility of ruthenium carbene complexes confer them a great ability to catalyze domino processes. For this reason, the combination of metathesis reactions with additional transformations in a domino fashion has been exploited extensively, with the result of expanding the utility of ruthenium carbene complexes beyond that of just olefin metathesis. Among those domino processes, it is worth mentioning the sequence of cross-metathesis/intramolecular Michael addition, which allows for the generation of a wide variety of carbo- and heterocycles in a very simple manner, taking advantage of the benefits of domino reactions. Carbon-, oxygen- and nitrogen-centered nucleophiles are good partners in this protocol, the versatility of which has been illustrated with the synthesis of several biologically important compounds.1 Introduction2 Cross Metathesis/Intramolecular Aza-Michael Addition Sequences3 Cross Metathesis/Intramolecular Oxa-Michael Addition Sequences4 Cross Metathesis/Intramolecular Michael Addition Sequences5 Conclusions and Outlook

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Dragutan, V., I. Dragutan, and A. T. Balaban. "Metathesis Catalysed by the Platinum Group Metals." Platinum Metals Review 44, no. 3 (July 1, 2000): 112–18. http://dx.doi.org/10.1595/003214000x443112118.

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In the first part of this review, published in the April issue of this Journal, the main catalyst systems used for metathesis catalysis were examined, and followed by a short report on metathesis activity and selectivity. In this second part, attention is now drawn to specific applications of platinum group metals metathesis catalysts, in particular, to a variety of ring-closing metathesis reactions. The last part of this review will be published in the October issue of this Journal.

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36

Malla, Raj K., Jeremy N. Ridenour, and Christopher D. Spilling. "Relay cross metathesis reactions of vinylphosphonates." Beilstein Journal of Organic Chemistry 10 (August 19, 2014): 1933–41. http://dx.doi.org/10.3762/bjoc.10.201.

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Dimethyl (β-substituted) vinylphosphonates do not readily undergo cross metathesis reactions with Grubbs catalyst and terminal alkenes. However, the corresponding mono- or diallyl vinylphosphonate esters undergo facile cross metathesis reactions. The improved reactivity is attributed to a relay step in the cross metathesis reaction mechanism.

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37

Salem Alqahtani, Mufleh. "Phonological Derivations of Synchronic Metathesis in Modern Persian." Advances in Language and Literary Studies 9, no. 4 (August 31, 2018): 92. http://dx.doi.org/10.7575/aiac.alls.v.9n.4p.92.

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This study discusses phonological derivations in Modern Persian which result from synchronic metathesis in light of Optimality Theory (OT). Synchronic metathesis to follow the Sonority Sequencing Principle (SSP) is operated by two phonological rules; metathesis of word-final cluster and Sonority-Driven epenthesis. In this context, the first rule blocks the environment for the second. This phonological derivation is known as bleeding which is also a type of phonological derivation of synchronic metathesis that is motivated by the Syllable Contact Law. The first rule, as the metathesis of heterosyllabic consonants, blocks the environment for the second, as in contact anaptyxis. OT Parallelism is capable of accounting for this bleeding as a transparent rule interaction yielded by synchronic metathesis, which is motivated by the Syllable Contact Law as well as the SSP since reference to the intermediate steps between input and output is not necessary. To that end OT Parallelism is capable of accounting for transparency in the bleeding order.

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38

Behr, Arno, and Jessica Pérez Gomes. "The cross-metathesis of methyl oleate with cis-2-butene-1,4-diyl diacetate and the influence of protecting groups." Beilstein Journal of Organic Chemistry 7 (January 3, 2011): 1–8. http://dx.doi.org/10.3762/bjoc.7.1.

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Background: α,ω-Difunctional substrates are useful intermediates for polymer synthesis. An attractive, sustainable and selective (but as yet unused) method in the chemical industry is the oleochemical cross-metathesis with preferably symmetric functionalised substrates. The current study explores the cross-metathesis of methyl oleate (1) with cis-2-butene-1,4-diyl diacetate (2) starting from renewable resources and quite inexpensive base chemicals. Results: This cross-metathesis reaction was carried out with several phosphine and N-heterocyclic carbene ruthenium catalysts. The reaction conditions were optimised for high conversions in combination with high cross-metathesis selectivity. The influence of protecting groups present in the substrates on the necessary catalyst loading was also investigated. Conclusions: The value-added methyl 11-acetoxyundec-9-enoate (3) and undec-2-enyl acetate (4) are accessed with nearly quantitative oleochemical conversions and high cross-metathesis selectivity under mild reaction conditions. These two cross-metathesis products can be potentially used as functional monomers for diverse sustainable polymers.

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Lemcoff, N., and Or Eivgi. "Turning the Light On: Recent Developments in Photoinduced Olefin Metathesis." Synthesis 50, no. 01 (September 21, 2017): 49–63. http://dx.doi.org/10.1055/s-0036-1589113.

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Olefin metathesis is one of the most important methods to form carbon–carbon double bonds and has found many applications in industry and academia. The ability to initiate the reaction using external stimulus such as light, with high spatial and temporal resolution is highly advantageous and provides creative novel opportunities in organic syntheses and material sciences. This review article covers recent advances in light-activated olefin metathesis reactions from the development of novel complexes that can be initiated photochemically to recently reported applications of photoinduced olefin metathesis, as well as the bright newly emerging field of photoredox-mediated metal-free ROMP.1 Introduction2 Light-Activated Olefin Metathesis Complexes2.1 Sulfur-Chelated Hoveyda–Grubbs-Type Complexes2.2 Nitrogen-Chelated Hoveyda–Grubbs-Type Complexes2.3 Catalyst Activation with Photoacid Generators2.4 Phototuning of Active Complexes2.5 Photoactivation of Non-Grubbs-Type Olefin Metathesis Complexes3 Photoredox-Mediated Metal-Free ROMP4 Applications of Photoinduced Olefin Metathesis4.1 Chromatic Orthogonal Olefin Metathesis4.2 UV-Filter-Assisted Olefin Metathesis4.3 Photolithographic Olefin Metathesis Polymerization5 Conclusions

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Kotha, Sambasivarao, Milind Meshram, and Chandravathi Chakkapalli. "Synergistic approach to polycycles through Suzuki–Miyaura cross coupling and metathesis as key steps." Beilstein Journal of Organic Chemistry 14 (September 21, 2018): 2468–81. http://dx.doi.org/10.3762/bjoc.14.223.

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This account provides an overview of recent work, including our own contribution dealing with Suzuki–Miyaura cross coupling in combination with metathesis (or vice-versa). Several cyclophanes, polycycles, macrocycles, spirocycles, stilbenes, biaryls, and heterocycles have been synthesized by employing a combination of Suzuki cross-coupling and metathesis. Various popular reactions such as Diels–Alder reaction, Claisen rearrangement, cross-metathesis, and cross-enyne metathesis are used. The synergistic combination of these powerful reactions is found to be useful for the construction of complex targets and fulfill synthetic brevity.

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41

Żak, Patrycja, and Cezary Pietraszuk. "Application of olefin metathesis in the synthesis of functionalized polyhedral oligomeric silsesquioxanes (POSS) and POSS-containing polymeric materials." Beilstein Journal of Organic Chemistry 15 (February 4, 2019): 310–32. http://dx.doi.org/10.3762/bjoc.15.28.

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This mini-review summarizes the applications of olefin metathesis in synthesis and functionalization of polyhedral oligomeric silsesquioxanes (POSS) and POSS-containing polymeric materials. Three types of processes, i.e., cross metathesis (CM) of vinyl-substituted POSS with terminal olefins, acyclic diene metathesis (ADMET) copolymerization of divinyl-substituted POSS with α,ω-dienes and ring-opening metathesis polymerization (ROMP) of POSS-substituted norbornene (or other ROMP susceptible cycloolefins) are discussed. Emphasis was put on the synthetic and catalytic aspects rather than on the properties and applications of synthesized materials.

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42

Duménil, Annie. "A Rule-Account of Metathesis in Gascon." Lingvisticæ Investigationes. International Journal of Linguistics and Language Resources 11, no. 1 (January 1, 1987): 81–113. http://dx.doi.org/10.1075/li.11.1.04dum.

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This paper presents a systematic diachronic study of metathesis in Gascon, in dialect of Occitan. A method of weighing syllables is proposed to arrive at a rule-account of metathesis and the analysis is based on the claim that the difference in weight between two contiguous syllables can explain the metathesis process. The syllable weight approach is shown to apply to all instances and absences of metathesis in Gascon and is able to predict its occurrence under a single rule accounting for all possibly relevant environments.

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Maurya, Sushil K., Mark Dow, Stuart Warriner, and Adam Nelson. "Synthesis of skeletally diverse alkaloid-like molecules: exploitation of metathesis substrates assembled from triplets of building blocks." Beilstein Journal of Organic Chemistry 9 (April 22, 2013): 775–85. http://dx.doi.org/10.3762/bjoc.9.88.

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A range of metathesis substrates was assembled from triplets of unsaturated building blocks. The approach involved the iterative attachment of a propagating and a terminating building block to a fluorous-tagged initiating building block. Metathesis cascade chemistry was used to “reprogram” the molecular scaffolds. Remarkably, in one case, a cyclopropanation reaction competed with the expected metathesis cascade process. Finally, it was demonstrated that the metathesis products could be derivatised to yield the final products. At each stage, purification was facilitated by the presence of a fluorous-tagged protecting group.

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Rybáčková, Markéta, Jan Hošek, Ondřej Šimůnek, Viola Kolaříková, and Jaroslav Kvíčala. "Computational study of productive and non-productive cycles in fluoroalkene metathesis." Beilstein Journal of Organic Chemistry 11 (November 10, 2015): 2150–57. http://dx.doi.org/10.3762/bjoc.11.232.

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A detailed DFT study of the mechanism of metathesis of fluoroethene, 1-fluoroethene, 1,1-difluoroethene, cis- and trans-1,2-difluoroethene, tetrafluoroethene and chlorotrifluoroethene catalysed with the Hoveyda–Grubbs 2nd generation catalyst was performed. It revealed that a successful metathesis of hydrofluoroethenes is hampered by a high preference for a non-productive catalytic cycle proceeding through a ruthenacyclobutane intermediate bearing fluorines in positions 2 and 4. Moreover, the calculations showed that the cross-metathesis of perfluoro- or perhaloalkenes should be a feasible process and that the metathesis is not very sensitive to stereochemical issues.

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45

Polyanskii, Kirill B., Kseniia A. Alekseeva, Pavel V. Raspertov, Pavel A. Kumandin, Eugeniya V. Nikitina, Atash V. Gurbanov, and Fedor Ivanovich Zubkov. "Hoveyda–Grubbs catalysts with an N→Ru coordinate bond in a six-membered ring. Synthesis of stable, industrially scalable, highly efficient ruthenium metathesis catalysts and 2-vinylbenzylamine ligands as their precursors." Beilstein Journal of Organic Chemistry 15 (March 22, 2019): 769–79. http://dx.doi.org/10.3762/bjoc.15.73.

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A novel and efficient approach to the synthesis of 2-vinylbenzylamines is reported. This involves obtaining 2-vinylbenzylamine ligands from tetrahydroisoquinoline by alkylation and reduction followed by the Hofmann cleavage. The resultant 2-vinylbenzylamines allowed us to obtain new Hoveyda–Grubbs catalysts, which were thoroughly characterised by NMR, ESIMS, and X-ray crystallography. The utility of this chemistry is further demonstrated by the tests of the novel catalysts (up to 10−2 mol %) in different metathesis reactions such as cross metathesis (CM), ring-closing metathesis (RCM) and ring-opening cross metathesis (ROCM).

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46

Dragutan, Valerian, and Ileana Dragutan. "Ruthenium Vinylidene Complexes." Platinum Metals Review 48, no. 4 (October 1, 2004): 148–53. http://dx.doi.org/10.1595/003214004x484148153.

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This paper surveys an attractive family of ruthenium complexes with great potential for applications in organic and polymer synthesis. When compared with traditional ruthenium alkylidene pre-catalysts, these alternative ruthenium vinylidene complexes are easily accessible from commercial starting materials. In addition, they display moderate to high metathesis activity and stability, and exhibit good tolerance towards an array of functional groups, air and moisture. Their synthesis, physical-chemical properties and catalytic attributes indicate they are quite promising initiators of efficient applications in ring-closing metathesis, cross metathesis and ring-opening metathesis polymerisation.

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47

Sauer, Daniel F., Johannes Schiffels, Takashi Hayashi, Ulrich Schwaneberg, and Jun Okuda. "Olefin metathesis catalysts embedded in β-barrel proteins: creating artificial metalloproteins for olefin metathesis." Beilstein Journal of Organic Chemistry 14 (November 19, 2018): 2861–71. http://dx.doi.org/10.3762/bjoc.14.265.

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This review summarizes the recent progress of Grubbs–Hoveyda (GH) type olefin metathesis catalysts incorporated into the robust fold of β-barrel proteins. Anchoring strategies are discussed and challenges and opportunities in this emerging field are shown from simple small-molecule transformations over ring-opening metathesis polymerizations to in vivo olefin metathesis.

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48

Pemba, Alexander G., and Stephen A. Miller. "Acetal Metathesis: Mechanistic Insight." Synlett 30, no. 17 (May 13, 2019): 1971–76. http://dx.doi.org/10.1055/s-0037-1611833.

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The origins and recent applications of acetal metathesis are discussed in the context of synthesizing polyacetals via acetal metathesis polymerization (AMP). A kinetic study of the acid-catalyzed acetal metathesis reaction suggests the rate = k[H+][acetal]2, with MeOCH2OMe and EtOCH2OEt interchanging to yield MeOCH2OEt, achieving the statistical 1:2:1 equilibrium distribution in 4 hours at 80 °C and in 1 hour at 90 °C. Upon heating 1,10-decanediol and diethoxymethane, polydecylene acetal is formed with sequential distillation of ethanol, followed by diethoxymethane. A full mechanism for this polymerization is proposed, which begins with a transacetalization sequence to convert the diol into a bisacetal, followed by acetal metathesis to yield a high-molecular-weight polymer.

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49

Hua, Derun, Zheng Zhou, Qianqian Hua, Jian Li, Xinning Lu, Yongrong Xie, Hong Xiao, Mei Li, and Jin Yang. "Transformation of 2-Butene into Propene on WO3/MCM-48: Metathesis and Isomerization of n-Butene." Catalysts 8, no. 12 (November 26, 2018): 585. http://dx.doi.org/10.3390/catal8120585.

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The metathesis of 2-butene (Trans and Cis) to propene was investigated over W-based catalysts. Thermodynamic calculations for metathesis and isomerization were carried out at various temperatures to test the reactions. The results showed that the WO3/MCM-48 catalyst had good catalytic activity. The metathesis activity depended on the acidity of the catalyst and the dispersity of the WO3 on the supports. High temperatures promoted the isomerization of 2-butene to 1-butene. According to thermodynamic analysis, however, this is adverse to the metathesis reaction, making it important to determine an appropriate reaction temperature.

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Abderrezak, Meriem K., Kristýna Šichová, Nancy Dominguez-Boblett, Antoine Dupé, Zahia Kabouche, Christian Bruneau, and Cédric Fischmeister. "Cross metathesis of unsaturated epoxides for the synthesis of polyfunctional building blocks." Beilstein Journal of Organic Chemistry 11 (October 8, 2015): 1876–80. http://dx.doi.org/10.3762/bjoc.11.201.

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The cross metathesis of 1,2-epoxy-5-hexene (1) with methyl acrylate and acrylonitrile was investigated as an entry to the synthesis of polyfunctional compounds. The resulting cross metathesis products were hydrogenated in a tandem fashion employing the residual ruthenium from the metathesis step as the hydrogenation catalyst. Interestingly, the epoxide ring remained unreactive toward this hydrogenation method. The saturated compound resulting from the cross metathesis of 1 with methyl acrylate was transformed by means of nucleophilic ring-opening of the epoxide to furnish a diol, an alkoxy alcohol and an amino alcohol in high yields.

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