Olefin Metathesis. Theory and Practice

  • ID: 2708347
  • Book
  • 608 Pages
  • John Wiley and Sons Ltd
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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.

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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 5Didier Astruc

Section II TYPES OF OLEFIN METATHESIS REACTIONS 37

2 Cross Metathesis 39Karolina Zukowska and Karol Grela

3 Ring–Closing Metathesis 85Bianca J. van Lierop, Justin A. M. Lummiss, and Deryn E. Fogg

4 Ene–Yne Metathesis 153Steven T. Diver and Justin R. Griffiths

5 Domino and Other Olefin Metathesis Reaction Sequences 187Bernd Schmidt and Stefan Krehl

6 Enantioselective Olefin Metathesis 233Brice Stenne and Shawn K. Collins

7 Olefin Metathesis Polymerization 269Astrid–Caroline Knall and Christian Slugovc

Section III APPLICATIONS OF OLEFIN METATHESIS REACTIONS 285

8 Applications in the Synthesis of Natural and Biologically Active Molecules 287Janine Cossy

9 Multifold Ring–Closing Olefin Metatheses in Syntheses of Organometallic Molecules with Unusual Connectivities 311Tobias Fiedler and John A. Gladysz

10 Industrial Applications of Olefin Metathesis Polymerization 329Christian Slugovc

11 Commercial Potential of Olefin Metathesis of Renewable Feedstocks 335Andrew Nickel and Richard L. Pederson

12 Challenges and Opportunities for Scaling the Ring–Closing Metathesis Reaction in the Pharmaceutical Industry 349Keith 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 371Cezary Pietraszuk

14 Ruthenium–Benzylidene Olefin Metathesis Catalysts 397Georgios C. Vougioukalakis

15 Ruthenium–Indenylidene and Other Alkylidene Containing Olefin Metathesis Catalysts 417César A. Urbina–Blanco, Stefano Guidone, Steven P. Nolan, and Catherine S. J. Cazin

16 Hoveyda–Type Olefin Metathesis Complexes 437Yakov Ginzburg and N. Gabriel Lemcoff

17 Schiff Base Catalysts and Other Related Latent Systems for Polymerization Reactions 453Yohann 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 475Micha³ Barbasiewicz

19 Theoretical Attempts: In Silico Olefin Metathesis How Can Computers Help in the Understanding of Metathesis Mechanisms and in Catalysts Development? 483Albert Poater, Laura Falivene, and Luigi Cavallo

20 Immobilization of Olefin Metathesis Catalysts 495Michael R. Buchmeiser

21 Olefin Metathesis inWater and Aqueous Media 515Bruce H. Lipshutz and Subir Ghorai

22 Olefin Metathesis in Green Organic Solvents and Without Solvent 523Christian Bruneau and Cédric Fischmeister

23 Olefin Metathesis in Fluorous Phases and in Fluorinated Aromatic Solvents 537Cezary Samoj³owicz, Anna Kajetanowicz, and Karol Grela

24 Olefin Metathesis in Ionic Liquids 547Pierre Queval, Mathieu Rouen, Annie–Claude Gaumont, Isabelle Dez, Olivier Baslé, and Marc Mauduit

25 Purification Strategies in Olefin Metathesis 559Krzysztof 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

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Karol Grela
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