Olefin Metathesis: Theory and Practice

Olefin Metathesis is a complete examination of the theory and methods behind one of the most widely used chemical reactions in research and industry. It provides basic information for non–specialists, while also explaining the latest trends and advancements in the field to experts. The coverage is broken into two parts. The first section discusses the various types of metathesis reactions, including CM, RCM, enyne metathesis, ROMP, and tandem processes, as well as their common applications. The second section 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. Included at the end of the book are catalyst–substrate compatibility charts, tables with structures and properties of commercial catalysts, NMR data, and recommendations for commercial 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.

Preface Contributor List Part I: Applications of Olefin Metathesis Reactions Section 1. Introduction Chapter 1. Olefin Metathesis Reactions: From a Historical Account to Recent Trends Didier Astruc Section 2. Types of Olefin Metathesis Reactions Chapter 2. Cross Metathesis Karolina ¯ukowska, and Karol Grela   Chapter 3. Ring–Closing Metathesis Bianca J. van Lierop, Justin A. M. Lummiss and Deryn E. Fogg  Chapter 4. Ene–Yne Metathesis Steven T. Diver and Justin R. Griffiths Chapter. 5. Domino and Other Olefin Metathesis Reaction Sequences Bernd Schmidt and Stefan Krehl Chapter 6. Enantioselective Olefin Metathesis Brice Stenne and Shawn K. Collins Chapter 7. Olefin Metathesis Polymerization Astrid–Caroline Knall and Christian Slugovc Section 3. Applications of Olefin Metathesis Reactions  Chapter 8. Applications in Synthesis of Natural and Biologically Active Molecules Janine Cossy Chapter 9. Multifold Ring Closing Olefin Metatheses in Synthesis of Organometallic Molecules with Unusual Connectivities Tobias Fiedler and John A. Gladysz Chapter 10. Industrial Applications of Olefin Metathesis Polymerization Christian Slugovc Chapter 11. Commercial Potential of Olefin Metathesis of Renewable Feedstocks Andrew Nickel and Richard L. Pederson Chapter 12. Challenges and Opportunities for Scaling the Ring Closing Metathesis Reaction in the Pharmaceutical Industry Keith R. Fandrick, Jolaine Savoie, Nathan Yee, Jinhua J. Song and Chris H. Senanayake Part II: Development of the Tools Section 4. Different Classes of Olefin Metathesis Catalysts Chapter 13. Well–Defined Olefin Metathesis Catalysts Based on Metals of Group 4–7 Cezary Pietraszuk Chapter 14. Ruthenium–Benzylidene Olefin Metathesis Catalysts Georgios C. Vougioukalakis Chapter 15. Ruthenium–Indenylidene and Other Alkylidene Containing Olefin Metathesis Catalysts César A. Urbina–Blanco, Stefano Guidone, Steven P. Nolan and Catherine S. J. Cazin Chapter 16. Hoveyda–Type Olefin Metathesis Catalysts Yakov Ginzburg and N. Gabriel Lemcoff Chapter 17 . Schiff Base Catalysts And Other Related Latent Systems for Polymerization Reactions Yohann Morin and Régis M. Gauvin  Section 5. Development of Concepts in Olefin Metathesis Catalysts Chapter 18. Novel Concepts in Catalyst Design—A Case Study Of Development of Hoveyda–Type Complexes Micha³ Barbasiewicz Chapter 19. Theoretical Attempts: “In Silico Olefin Metathesis”—How Can Computers Help in Understanding of Metathesis Mechanisms and in Catalysts Development? Albert Poater, Laura Falivene and Luigi Cavallo Chapter 20. Immobilization of Olefin Metathesis Catalysts Michael R. Buchmeiser Chapter 21. Olefin Metathesis in Water and Aqueous Media Bruce H. Lipshutz, and Subir Ghorai Chapter 22. Olefin Metathesis in Green Organic Solvents and Without Solvent Christian Bruneau, and Cédric Fischmeister Chapter 23. Olefin Metathesis in Fluorous Phases and in Fluorinated Aromatic Solvents Cezary Samoj³owicz, Anna Kajetanowicz and Karol Grela  Chapter 24. Olefin Metathesis in Ionic Liquids Pierre Queval, Mathieu Rouen, Annie–Claude Gaumont, Isabelle Dez, Olivier Baslé and Marc Mauduit Chapter 25. Purification Strategies in Olefin Metathesis Krzysztof Skowerski and £ukasz Gu³ajski   Part III: Tables and Charts Section 6. Olefin Metathesis Catalysts—A Tabular Review £ukasz Wo niak, Grzegorz Zieliñski and Karol Grela

Karol Grela is  Professor at the Institute of Organic Chemistry, Polish Academy of Sciences and 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 .