Organometallic Mechanisms and Catalysis

PrefaceGlossaryAbbreviations Chapter 1 Metal Catalysis in Organic Chemistry References Additional Reading Part One Oxidation-Reduction Processes Chapter 2 Homolytic Processes in Organic Oxidation-Reduction with Metal Complexes I. Oxidation-Reduction between Inorganic Complexes II. Oxidation-Reduction of Organic Compounds by Metal Complexes III. Redox Chain Reactions in Metal-Catalyzed Processes References Additional Reading Chapter 3 Organometal Free Radicals I. Structural Types II. Metal-Centered Radicals III. Multicentered Radicals IV. Carbon-Centered Organometal Radicals V. Free Radical-Metal Complexes References Additional Reading Chapter 4 Catalytic Reactions of Peroxides I. Homolytic Mechanisms in Metal Catalysis II. Heterolytic Mechanisms in Metal Catalysis References Additional Reading Chapter 5 Metal Complexes in Organic Oxidations I. Direct Oxidation II. Catalytic Oxidations References Additional Reading Chapter 6 Metal-Catalyzed Addition to Olefins References Additional Reading Chapter 7 Reduction of Organic Halides I. Chromium(II) and Cobalt(H) Reduction by Halogen Atom Transfer II. Electron Transfer Reduction of Organic Halides III. Radical Chain Processes in the Reduction of Alkyl Halides IV. Reductions by Transition Metal Complexes: Oxidative Addition References Additional Reading Chapter 8 Transition Metal Carbonyls I. Ligand Substitution II. Activation of Molecular Hydrogen III. Hydrogen Transfer in Hydrido Carbonyl Metals IV. Dissociation of Binuclear Carbonyl Metals V. Oxidation of Carbonyl Metals VI. Additions to Olefins VII. Carbonylmetallate Anions References Additional Reading Chapter 9 Metal-Catalyzed Reactions of Aromatic Diazonium Salts and Diazo Compounds I. Aromatic Diazonium Salts II. Diazo Compounds References Additional ReadingPart Two Chemistry of Organometals Chapter 10 Stability of Organometals I. Stable Alkylmetals II. Thermal Decompositions of Organometals III. Mechanistic Classifications for Thermolysis of Alkylmetals IV. Alkylmetals as Intermediates in Catalytic Reactions References Additional Reading Chapter 11 Thermochemistry of Organometals References Additional Reading Chapter 12 Concerted Two-Equivalent Processes for the Decomposition of Alkylmetals I. ß-Elimination of Alkyl Ligands II. Reductive Coupling of Alkyl Ligands III. Reductive Disproportionation and Coupling as Competing Pathways IV. α-Elimination of Alkylmetals V. Hydrogen and Alkyl Transfers to Alkylmetals References Additional Reading Chapter 13 Homolytic Pathways in the Reactions of Alkylmetals I. Introduction II. ß-Elimination of Alkyl Ligands III. Reductive Coupling of Alkyl Ligands IV. α-Elimination of Alkyl Ligands V. Hydrogen Transfer to Alkyl Ligands VI. Displacement Reactions in Alkylmetals References Chapter 14 Catalytic Processes for the Formation of Carbon-Carbon Bonds I. Alkyl Coupling versus Alkyl Disproportionation in Kharasch Reactions II. Copper Catalysis in the Cross Coupling of Alkyl Groups III. Iron Catalysis in the Cross Coupling of Alkenyl Halides IV. Nickel Catalysis in Cross-Coupling Reactions of Aryl and Vinyl Halides V. Cross Coupling with Allylic Groups VI. Alkyl Coupling by Insertion into Carbon-Carbon Multiple Bonds VII. Palladium and Rhodium Catalysis of Homo Coupling VIII. Carbonylation Reactions IX. Cyclooligomerization of Olefins and Acetylenes References Additional Reading Part Three Charge Transfer Interactions of Organometals Chapter 15 Organometals as Electron Donors I. Electron Transfer Processes II. Charge Transfer Interactions III. Ionization Potentials of Organometals IV. Charge Transfer Spectra of Organometals with Tetracyanoethylene V. Charge Transfer Interactions Leading to Electron Transfer VI. Operational Distinction between Electron Transfer and Charge Transfer Processes in Reactions of Organometals References Additional Reading Chapter 16 Electron Transfer and Charge Transfer Processes in the Cleavage of Alkylmetals I. Electron Transfer Cleavage of Organometals with Hexachloroiridate(IV) II. Charge Transfer Addition of Organometals to Tetracyanoethylene III. Other Reactions of Organometals Involving Electron Transfer or Charge Transfer IV. Charge Transfer, Electron Transfer, and Concerted Processes for the Reactions of Organometals References Additional Reading Chapter 17 Charge Transfer Interactions in the Reactions of Organometals with Acceptors I. Introduction II. Reactions of Organometals with Organic Halides III. Reactions of Organometals with Quinones IV. Grignard Reagents with Carbonyl Compounds V. Reactions of Organometals with Oxygen and Peroxides VI. Reactions of Organometals with Nitro Compounds References Additional Reading Chapter 18 Reactions of Organometals with Electrophiles I. Introduction II. Cleavage Reactions of Electrophiles III. Insertion Reactions of Electrophiles IV. Delineation of Electrophilic and Electron Transfer Mechanisms: A Summing Up References Additional Reading EpilogueIndex