Organometallic Chemistry

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  • Edition: 2nd
  • Format: Hardcover
  • Copyright: 2009-10-26
  • Publisher: Oxford University Press
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Spessard and Miessler's Organometallic Chemistry, originally published by Prentice Hall in 1997, is widely acknowledged as the most appropriate text for undergraduates and beginning graduate students taking this course. It is a highly readable and approachable text that starts with the basicinorganic chemistry needed to understand this advanced topic. Unlike the primary competing book by Crabtree (Wiley), S/M places a strong emphasis on structure and bonding in the first several chapters, which lay the foundation for later discussion of reaction types and applications. Theorganization of material is much more accessible for students who have never seen organometallic chemistry before. In addition to being pitched at the right level for undergraduate students, S/M presents outstanding explanations of important core topics such as molecular orbitals and bonding andsupports these discussions with detailed illustrations and praised end of chapter problems. The second edition has been significantly revised and updated to include advancements over the last ten years in NMR, IR spectroscopy, nanotechnology and physical methods. The authors have significantly updated four chapters (9, 10, 11 and 12). Chapter 9 (catalysis) has been revised to cover theadvances in catalytic cycle research. Chapter 10 in the first edition, which covered carbene complexes, metathesis, and polymerization, has been divided into two chapters in view of the expanded research efforts that have occurred over the last ten years in these areas. Chapter 10 in the secondedition now focuses on carbene complexes, and Chapter 11 covers aspects of metathesis and polymerization reactions including an expanded discussion of Schrock and Grubbs metal carbene catalysts. Chapter 12 (Chapter 11, first edition) is a substantially-revised treatment of the applications oforganometallic chemistry to organic synthesis. This chapter offers an extensive discussion of asymmetric hydrogenation and oxidation methodology as well as a greatly revised treatment of Tsuji-Trost allylation, the Heck reaction, and palladium-catalyzed cross-coupling reactions. The latter topicincludes discussion of the Stille, Suzuki, Sonogashira, and Negishi cross-couplings, reactions that have had a profound impact on the synthesis of anti-tumor compounds and other potent pharmaceuticals. In addition, the authors have included more molecular model illustrations, and introduced more modern examples and medical/medicinal applications across the text. They have included 53% more in-chapter exercises and end-of-chapter problems (23% more exercises and 81% more EOCs). The second editionhas been extensively updated to include current literature (62% more references to the chemical literature).

Table of Contents

Figuresp. xi
Prefacep. xvii
An Overview of Organometallic Chemistry
Striking Differencep. 1
Historical Backgroundp. 4
Fundamentals of Structure and Bondingp. 13
Atomic Orbitalsp. 13
Molecular Orbitalsp. 21
Computational Organometallic Chemistryp. 42
The 18-Electron Rulep. 53
Counting Electronsp. 53
Why 18 Electrons?p. 60
Square Planar Complexesp. 69
The Carbonyl Ligandp. 75
Bondingp. 75
Binary Carbonyl Complexesp. 83
Oxygen-Bonded Carbonylsp. 86
Ligands Similar to COp. 87
IR Spectrap. 92
Main Group Parallels with Binary Carbonyl Complexesp. 96
Pi Ligandsp. 103
Linear Pi Systemsp. 103
Cyclic ? Systemsp. 107
Nuclear Magnetic Resonance Spectra of Organometallic Compoundsp. 127
Other Important Ligandsp. 136
Complexes Containing M-C, M=C, and M=C Bondsp. 136
Hydride and Dihydrogen Complexesp. 152
Phosphines and Related Ligandsp. 155
Fullerene Ligandsp. 160
Mass Spectrap. 165
Organometallic Reactions I: Reactions That Occur at the Metalp. 176
Ligand Substitutionp. 178
Oxidative Additionp. 202
Reductive Eliminationp. 226
Organometallic Reactions II: Reactions Involving Modification of Ligandsp. 244
Insertion and Deinsertionp. 244
Nucleophilic Addition to the Ligandp. 267
Nucleophilic Abstractionp. 285
Electrophilic Reactionsp. 289
Homogeneous Catalysis: The Use of Transition Metal Complexes in Catalytic Cyclesp. 311
Fundamental Concepts of Homogeneous Catalysisp. 312
The Hydroformylation Reactionp. 322
The Wacker-Smidt Synthesis of Acetaldehydep. 340
Hydrogenationp. 350
Carbonylation of Methanolp. 361
Hydrocyanationp. 367
Specialty Chemicalsp. 375
Transition Metal-Carbene and-Carbyne Complexes: Structure, Preparation, and Chemistryp. 393
Structure of Metal Carbenesp. 394
Synthesis of Metal Carbene Complexesp. 407
Reactions of Metal-Carbene Complexesp. 419
Metal-Carbyne Complexesp. 439
sMetathesis and Polymerization Reactionsp. 456
Bond Metathesisp. 456
Alkyne Metathesisp. 486
Ziegler-Natta and Related Polymerizations of Alkenesp. 492
Bond Metathesisp. 507
Applications of Organometallic Chemistry to Organic Synthesisp. 522
Enantioselective Functional Group Interconversionsp. 524
Carbon-Carbon Bond Formation via Nucleophilic Attack on an 3- Ligand: The Tsuji-Trost Reactionp. 555
Carbon-Carbon Bond Formation via Carbonyl and Alkene Insertionp. 567
Carbon-Carbon Bond Formation via Transmetalation Reactions (Cross-Coupling Reactions)p. 584
Carbon-Carbon Bond Formation through Cyclization Reactionsp. 613
Isolobal Groups and Cluster Compoundsp. 640
The Isolobal Analogyp. 640
Cluster Compoundsp. 650
List of Abbreviationsp. A-1
Answers to Exercisesp. A-5
Indexp. I-1
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