A complete examination of modern olefin metathesis, one of the most widely used chemical reactions Garnering the 2005 Nobel Prize in chemistry for its discoverers, olefin metathesis has gained widespread use in research and industry for making products like medicines, polymers, and enhanced fuels. Olefin Metathesis offers a comprehensive analysis of the field, providing basic and necessary information for non-specialists while explaining the latest trends and advancements for experts. Acting as a guidebook, chapters include in-depth discussion on essential topics: * Various types of metathesis…mehr
A complete examination of modern olefin metathesis, one of the most widely used chemical reactions Garnering the 2005 Nobel Prize in chemistry for its discoverers, olefin metathesis has gained widespread use in research and industry for making products like medicines, polymers, and enhanced fuels. Olefin Metathesis offers a comprehensive analysis of the field, providing basic and necessary information for non-specialists while explaining the latest trends and advancements for experts. Acting as a guidebook, chapters include in-depth discussion on essential topics: * Various types of metathesis reactions like CM, RCM, enyne metathesis, ROMP, and tandem processes, as well as their applications * Tools of the trade, from the important classes of active metal complexes to optimal reaction conditions * Tips to help chemists choose the right catalysts and determine substrate scope * Select and representative procedures for each metathesis class * Practical solutions and explanations for common reaction problems Included at the end of the book are tables with structures of commercial catalysts and recommendations for catalyst suppliers. With contributions from a multinational group of leading experts and practitioners in the field, this is an essential compendium for chemists at all levels.
KAROL GRELA is a Professor at the Institute of Organic Chemistry, Polish Academy of Sciences, and the Director of the Organometallic Synthesis Laboratory at the Biological and Chemical Research Centre of the Faculty of Chemistry, University of Warsaw, Poland. Having written over 100 peer-reviewed papers, he is on the editorial board of Chemistry--a European Journal and on the advisory board for the European Journal of Organic Chemistry and Organometallics.
Inhaltsangabe
PREFACE ix
CONTRIBUTORS xi
PART I APPLICATIONS OF OLEFIN METATHESIS REACTIONS 1
Section I INTRODUCTION 3
1 Olefin Metathesis Reactions: From a Historical Account toRecent Trends 5 Didier Astruc
Section II TYPES OF OLEFIN METATHESIS REACTIONS 37
2 Cross Metathesis 39 Karolina Zukowska and Karol Grela
3 Ring-Closing Metathesis 85 Bianca J. van Lierop, Justin A. M. Lummiss, and Deryn E.Fogg
4 Ene-Yne Metathesis 153 Steven T. Diver and Justin R. Griffiths
5 Domino and Other Olefin Metathesis Reaction Sequences187 Bernd Schmidt and Stefan Krehl
6 Enantioselective Olefin Metathesis 233 Brice Stenne and Shawn K. Collins
7 Olefin Metathesis Polymerization 269 Astrid-Caroline Knall and Christian Slugovc
Section III APPLICATIONS OF OLEFIN METATHESIS REACTIONS285
8 Applications in the Synthesis of Natural and BiologicallyActive Molecules 287 Janine Cossy
9 Multifold Ring-Closing Olefin Metatheses in Syntheses ofOrganometallic Molecules with Unusual Connectivities 311 Tobias Fiedler and John A. Gladysz
10 Industrial Applications of Olefin Metathesis Polymerization329 Christian Slugovc
11 Commercial Potential of Olefin Metathesis of RenewableFeedstocks 335 Andrew Nickel and Richard L. Pederson
12 Challenges and Opportunities for Scaling the Ring-ClosingMetathesis Reaction in the Pharmaceutical Industry 349 Keith R. Fandrick, Jolaine Savoie, Nathan Yee, Jinhua J. Song,and Chris H. Senanayake
PART II DEVELOPMENT OF THE TOOLS 367
Section IV DIFFERENT CLASSES OF OLEFIN METATHESIS CATALYSTS369
13 Well-Defined Olefin Metathesis Catalysts Based on Metals ofGroup 4-7 371 Cezary Pietraszuk
14 Ruthenium-Benzylidene Olefin Metathesis Catalysts 397 Georgios C. Vougioukalakis
15 Ruthenium-Indenylidene and Other Alkylidene Containing OlefinMetathesis Catalysts 417 César A. Urbina-Blanco, Stefano Guidone, Steven P. Nolan,and Catherine S. J. Cazin
16 Hoveyda-Type Olefin Metathesis Complexes 437 Yakov Ginzburg and N. Gabriel Lemcoff
17 Schiff Base Catalysts and Other Related Latent Systems forPolymerization Reactions 453 Yohann Morin and Régis M. Gauvin
Section V DEVELOPMENT OF CONCEPTS IN OLEFIN METATHESISCATALYSTS 473
18 Novel Concepts in Catalyst Design--a Case Study ofDevelopment of Hoveyda-Type Complexes 475 Micha³ Barbasiewicz
19 Theoretical Attempts: "In Silico OlefinMetathesis"--How Can Computers Help in the Understandingof Metathesis Mechanisms and in Catalysts Development? 483 Albert Poater, Laura Falivene, and Luigi Cavallo
20 Immobilization of Olefin Metathesis Catalysts 495 Michael R. Buchmeiser
21 Olefin Metathesis inWater and Aqueous Media 515 Bruce H. Lipshutz and Subir Ghorai
22 Olefin Metathesis in Green Organic Solvents and WithoutSolvent 523 Christian Bruneau and Cédric Fischmeister
23 Olefin Metathesis in Fluorous Phases and in FluorinatedAromatic Solvents 537 Cezary Samoj³owicz, Anna Kajetanowicz, and KarolGrela
24 Olefin Metathesis in Ionic Liquids 547 Pierre Queval, Mathieu Rouen, Annie-Claude Gaumont, IsabelleDez, Olivier Baslé, and Marc Mauduit
25 Purification Strategies in Olefin Metathesis 559 Krzysztof Skowerski and £ukasz Gu³ajski
PART III TABLES AND CHARTS 573
Section VI OLEFIN METATHESIS CATALYSTS--A TABULAR REVIEW575 £ukasz Wo´zniak, Grzegorz Zieli´nski, andKarol Grela
PART I APPLICATIONS OF OLEFIN METATHESIS REACTIONS 1
Section I INTRODUCTION 3
1 Olefin Metathesis Reactions: From a Historical Account toRecent Trends 5 Didier Astruc
Section II TYPES OF OLEFIN METATHESIS REACTIONS 37
2 Cross Metathesis 39 Karolina Zukowska and Karol Grela
3 Ring-Closing Metathesis 85 Bianca J. van Lierop, Justin A. M. Lummiss, and Deryn E.Fogg
4 Ene-Yne Metathesis 153 Steven T. Diver and Justin R. Griffiths
5 Domino and Other Olefin Metathesis Reaction Sequences187 Bernd Schmidt and Stefan Krehl
6 Enantioselective Olefin Metathesis 233 Brice Stenne and Shawn K. Collins
7 Olefin Metathesis Polymerization 269 Astrid-Caroline Knall and Christian Slugovc
Section III APPLICATIONS OF OLEFIN METATHESIS REACTIONS285
8 Applications in the Synthesis of Natural and BiologicallyActive Molecules 287 Janine Cossy
9 Multifold Ring-Closing Olefin Metatheses in Syntheses ofOrganometallic Molecules with Unusual Connectivities 311 Tobias Fiedler and John A. Gladysz
10 Industrial Applications of Olefin Metathesis Polymerization329 Christian Slugovc
11 Commercial Potential of Olefin Metathesis of RenewableFeedstocks 335 Andrew Nickel and Richard L. Pederson
12 Challenges and Opportunities for Scaling the Ring-ClosingMetathesis Reaction in the Pharmaceutical Industry 349 Keith R. Fandrick, Jolaine Savoie, Nathan Yee, Jinhua J. Song,and Chris H. Senanayake
PART II DEVELOPMENT OF THE TOOLS 367
Section IV DIFFERENT CLASSES OF OLEFIN METATHESIS CATALYSTS369
13 Well-Defined Olefin Metathesis Catalysts Based on Metals ofGroup 4-7 371 Cezary Pietraszuk
14 Ruthenium-Benzylidene Olefin Metathesis Catalysts 397 Georgios C. Vougioukalakis
15 Ruthenium-Indenylidene and Other Alkylidene Containing OlefinMetathesis Catalysts 417 César A. Urbina-Blanco, Stefano Guidone, Steven P. Nolan,and Catherine S. J. Cazin
16 Hoveyda-Type Olefin Metathesis Complexes 437 Yakov Ginzburg and N. Gabriel Lemcoff
17 Schiff Base Catalysts and Other Related Latent Systems forPolymerization Reactions 453 Yohann Morin and Régis M. Gauvin
Section V DEVELOPMENT OF CONCEPTS IN OLEFIN METATHESISCATALYSTS 473
18 Novel Concepts in Catalyst Design--a Case Study ofDevelopment of Hoveyda-Type Complexes 475 Micha³ Barbasiewicz
19 Theoretical Attempts: "In Silico OlefinMetathesis"--How Can Computers Help in the Understandingof Metathesis Mechanisms and in Catalysts Development? 483 Albert Poater, Laura Falivene, and Luigi Cavallo
20 Immobilization of Olefin Metathesis Catalysts 495 Michael R. Buchmeiser
21 Olefin Metathesis inWater and Aqueous Media 515 Bruce H. Lipshutz and Subir Ghorai
22 Olefin Metathesis in Green Organic Solvents and WithoutSolvent 523 Christian Bruneau and Cédric Fischmeister
23 Olefin Metathesis in Fluorous Phases and in FluorinatedAromatic Solvents 537 Cezary Samoj³owicz, Anna Kajetanowicz, and KarolGrela
24 Olefin Metathesis in Ionic Liquids 547 Pierre Queval, Mathieu Rouen, Annie-Claude Gaumont, IsabelleDez, Olivier Baslé, and Marc Mauduit
25 Purification Strategies in Olefin Metathesis 559 Krzysztof Skowerski and £ukasz Gu³ajski
PART III TABLES AND CHARTS 573
Section VI OLEFIN METATHESIS CATALYSTS--A TABULAR REVIEW575 £ukasz Wo´zniak, Grzegorz Zieli´nski, andKarol Grela
Outlook and Perspectives 587
INDEX 589
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