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Full Description
This is a complete examination of the theory and methods of modern olefin metathesis, one of the most widely used chemical reactions in research and industry.
Provides basic information for non-specialists, while also explaining the latest trends and advancements in the field to experts
Discusses the various types of metathesis reactions, including CM, RCM, enyne metathesis, ROMP, and tandem processes, as well as their common applications
Outlines the tools of the trade—from the important classes of active metal complexes to optimal reaction conditions—and suggests practical solutions for common reaction problems
Includes tables with structures of commercial catalysts, and recommendations for commercial catalyst suppliers
Contents
PREFACE ix
CONTRIBUTORS xi
PART I APPLICATIONS OF OLEFIN METATHESIS REACTIONS 1
Section I INTRODUCTION 3
1 Olefin Metathesis Reactions: From a Historical Account to Recent 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 Sequences 187
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 REACTIONS 285
8 Applications in the Synthesis of Natural and Biologically Active Molecules 287
Janine Cossy
9 Multifold Ring-Closing Olefin Metatheses in Syntheses of Organometallic Molecules with Unusual Connectivities 311
Tobias Fiedler and John A. Gladysz
10 Industrial Applications of Olefin Metathesis Polymerization 329
Christian Slugovc
11 Commercial Potential of Olefin Metathesis of Renewable Feedstocks 335
Andrew Nickel and Richard L. Pederson
12 Challenges and Opportunities for Scaling the Ring-Closing Metathesis 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 CATALYSTS 369
13 Well-Defined Olefin Metathesis Catalysts Based on Metals of Group 4-7 371
Cezary Pietraszuk
14 Ruthenium-Benzylidene Olefin Metathesis Catalysts 397
Georgios C. Vougioukalakis
15 Ruthenium-Indenylidene and Other Alkylidene Containing Olefin Metathesis 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 for Polymerization Reactions 453
Yohann Morin and Régis M. Gauvin
Section V DEVELOPMENT OF CONCEPTS IN OLEFIN METATHESIS CATALYSTS 473
18 Novel Concepts in Catalyst Design—a Case Study of Development of Hoveyda-Type Complexes 475
Micha³ Barbasiewicz
19 Theoretical Attempts: "In Silico Olefin Metathesis"—How Can Computers Help in the Understanding of 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 Without Solvent 523
Christian Bruneau and Cédric Fischmeister
23 Olefin Metathesis in Fluorous Phases and in Fluorinated Aromatic Solvents 537
Cezary Samoj³owicz, Anna Kajetanowicz, and Karol Grela
24 Olefin Metathesis in Ionic Liquids 547
Pierre Queval, Mathieu Rouen, Annie-Claude Gaumont, Isabelle Dez, 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 REVIEW 575
£ukasz Wo'zniak, Grzegorz Zieli'nski, and Karol Grela
Outlook and Perspectives 587
INDEX 589
