THE ORGANOMETALLIC CHEMISTRY OF THE TRANSITION METALS
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1 THE ORGANOMETALLIC CHEMISTRY OF THE TRANSITION METALS Second Edition ROBERT H. CRABTREE Yale University New Haven, Connecticut A Wiley-Interscience Publication JOHN WILEY & SONS New York / Chichester / Brisbane / Toronto / Singapore
2 CONTENTS List of Abbreviations 1 Introduction Werner Complexes / The Trans Effect / Soft versus Hard Ligands / The Crystal Field / The Ligand Field / Back Bonding / Electroneutrality / Types of Ligand / 18 References / 22 Problems / 22 2 GENERAL PROPERTIES OF ORGANOMETALLIC COMPLEXES The 18-Electron Rule / Limitations of the 18-Electron Rule / Electron Counting in Reactions / Oxidation State / Coordination Number and Geometry / Effects of Complexation / 38 xv ix
3 X CONTENTS 2.7 Different Metals / 40 References / 42 Problems / 42 3 METAL ALKYLS, ARYLS, AND HYDRIDES AND RELATED a-bonded LIGANDS The Stability of Transition Metal Alkyls and Aryls / The Preparation of Metal Alkyls / Characterization and Properties of Metal Alkyls / Related cr-bonded Ligands / Metal Hydride Complexes / Bond Strengths for Classical cr-bonding Ligands / 66 References / 69 Problems / 70 4 CARBONYLS, PHOSPHINE COMPLEXES, AND LIGAND SUBSTITUTION REACTIONS Metal Complexes of CO, RNC, CS, and NO / Phosphines as Ligands / Dissociative Substitution / The Associative Mechanism / Redox Effects, The I Mechanism, and Rearrangements in Substitution / Photochemical Substitution / Steric and Solvent Effects in Substitution / 98 References / 102 Problems / COMPLEXES OF TT-BOUND LIGANDS Alkene and Alkyne Complexes / Allyl Complexes / Diene Complexes / Cyclopentadienyl Complexes / Complexes of Arenes and Other Alicyclic Ligands / Metalacycles and Isoelectronic and Isolobal Replacement / Stability of Polyene and Polyenyl Complexes / 134 References / 136 Problems / 138
4 CONTENTS Xi 6 OXIDATIVE ADDITION AND REDUCTIVE ELIMINATION Three-Center Additions / S N 2 Reactions / Radical Mechanisms / Ionic Mechanisms / Reductive Elimination / Oxidative Coupling and Reductive Cleavage / 155 References / 158 Problems / INSERTION AND ELIMINATION Reactions Involving CO / Insertions Involving Alkenes / Other Insertions / a, ß, 7, and 8 Elimination / 174 References / 178 Problems / NUCLEOPHILIC AND ELECTROPHILIC ADDITION AND ABSTRACTION Nucleophilic Addition to CO / Nucleophilic Addition to Polyene and Polyenyl Ligands / Nucleophilic Abstraction in Hydrides, Alkyls, and Acyls / Electrophilic Addition to the Metal / Electrophilic Abstraction of Alkyl Groups / Single-Electron Transfer Pathways / Reactions of Organic Free Radicals with Metal Complexes / 201 References / 202 Problems / HOMOGENEOUS CATALYSIS Alkene Isomerization / Alkene Hydrogenation / Alkene Hydroformylation / The Hydrocyanation of Butadiene / 226
5 XÜ CONTENTS 9.5 Alkene Hydrosilation and Hydroboration / 229 References / 232, Problems / CHARACTERIZATION OF ORGANOMETALLIC COMPOUNDS Isolation / 'H NMR Spectroscopy / ,3 C NMR Spectroscopy / P NMR Spectroscopy / Dynamic NMR / Spin Saturation Transfer / T { and NOE / Isotopic Perturbation of Resonance / IR Spectroscopy / Crystallography / Other Methods / 263 References / 266 Problems / CARBENES, METATHESIS, AND POLYMERIZATION Metal Carbenes / Metal Carbynes / Bridging Carbenes and Carbynes / Alkyne Metathesis / Alkene Polymerization and Oligomerization / Multiple Bonds to Heteroatoms / 302 References / 306 Problems / THE ACTIVATION OF SMALL MOLECULES CO Activation / C0 2 Activation / Alkane Activation / 321 References / 330 Problems / CLUSTERS AND THE METAL-METAL BOND Structures / The Isolobal Analogy / 348
6 CONTENTS XÜi 13.3 Synthesis / Reactions / Giant Clusters / 363 References / 366 Problems / APPLICATIONS TO ORGANIC SYNTHESIS Metal Alkyls and Hydrides / Reduction,Oxidation,andControlof Stereochemistry / Protection and Deprotection / Reductive Elimination / Coupling Reactions / Insertion Reactions / Nucleophilic Attack on a Ligand / Carbene Reactions / 407 References / 408 Problems / OXIDATION AND HIGH-OXIDATION-STATE COMPLEXES Polyalkyls / Polyhydrides / Cyclopentadienyl Complexes / Alkyne Complexes / 424 References / 426 Problems / BIOORGANOMETALLIC CHEMISTRY Introduction / Coenzyme B l2 / Nitrogen Fixation / The Nickel Enzymes / 446 References / 454 Problems / 455 USEFUL TEXTS ON ALLIED TOPICS 457 MAJOR REACTION TYPES 460 SOLUTIONS TO PROBLEMS 462 INDEX 477
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