Basic Organometallic Chemistry

Part I 18
1. Introduction 20
1.1. The Scope of Organometallic Chemistry 20
1.2. Some Historical Notes 21
1.3. The Classification of Organometallic Compounds 22
2.1 Bond Types 24
Ionic Bonds 24
2. The Metal-Carbon Bond 24
Dative Bonds, with d-Orbital participation (Sigma Donor - Pi Acceptor) 25
Electron-Deficient Bonds (Localized Polycentric Bonds) 25
Delocalized Bonds in Polynuclear Systems 25
Sigma Covalent Bonds (Bicentric Bielectronic) 25
2.2. Metal-Carbon Ionic Bonds 26
2.3. Sigma (σ ) Covalent Bonds (Bicentric Bielectronic) 29
2.4. Electron-Deficient Bonds (Polycentric Localized-Bonds) 31

Part I 18
1. Introduction 20
1.1. The Scope of Organometallic Chemistry 20
1.2. Some Historical Notes 21
1.3. The Classification of Organometallic Compounds 22
2.1 Bond Types 24
Ionic Bonds 24
2. The Metal-Carbon Bond 24
Dative Bonds, with d-Orbital participation (Sigma Donor - Pi Acceptor) 25
Electron-Deficient Bonds (Localized Polycentric Bonds) 25
Delocalized Bonds in Polynuclear Systems 25
Sigma Covalent Bonds (Bicentric Bielectronic) 25
2.2. Metal-Carbon Ionic Bonds 26
2.3. Sigma (σ ) Covalent Bonds (Bicentric Bielectronic) 29
2.4. Electron-Deficient Bonds (Polycentric Localized-Bonds) 31
2.5. Delocalized Bonds in Polynuclear Systems 33
2.6. Dative Bonds with Participation of d-Orbitals 35
3. Laboratory Techniques in Organometallic Chemistry 46
3.1. Synthesis and Isolation of Compounds 46
3.2. Analysis and Structural Characterization 50
4. The Literature of Organometallic Chemistry 52
4.1. Textbooks and General Monographs 53
4.2. Reviews 54
4.3. Primary Literature 55
Part II Organometallic Compounds of Non-Transition Elements 60
5. Organometallic Compounds of Alkali Metals 62
5.1. Organolithium Compounds 62
5.2. Organometallic Derivatives of Sodium and the Heavier Alkali Metals 68
6. Organometallic Compounds of the Group II Elements 72
6.1. Organoberyllium Compounds 73
6.2. Organomagnesium Compounds 79
6.3. Organometallic Compounds of Calcium, Strontium and Barium 83
6.4. Organozinc Compounds 84
6.5. Organocadmium Derivatives 88
6.6. Organomercury Compounds 91
7. Organometallic Compounds of Group III A Elements 98
7.1. Organoboron Compounds 99
7.2. Organoaluminum Compounds 114
7.3. Organogallium Compounds 121
Diorganoindium Halides, R2InX 126
7.4. Organoindium Compounds 126
Trisubstituted Derivatives, InR3 126
Organoindium Dihalides, RInX2 127
7.5. Organothallium Compounds 128
8. Organometallic Compounds of Group IVA Elements 132
8.1. Organosilicon Compounds 133
8.2. Organogermanium Compounds 160
8.3. Organotin Compounds 170
8.4. Organolead Compounds 190
9. Organometallic Compounds of Group VA Elements 200
9.1. Organoarsenic Compounds 200
9.2. Organoantimony Compounds 222
9.3. Organobismuth Compounds 233
Part III Organometallic Compounds of Transition Metals 238
10. The Electronic Structure and Classification of Transition-Metal Organometallic Compounds 240
10.1 The Transition Metals 240
10.2. The Ligands 241
11. Compounds with Two-Electron Ligands 244
11.1. Metal Carbonyls 244
11.2. Metal Thiocarbonyls 266
11.3. Metal Selenocarbonyls 267
11.4. Metal-Isocyanide Complexes 267
11.5. Metal-Carbene Complexes and Related Compounds 269
11.6. π -Olefinic Complexes 272
12.1. π -Allylic Complexes and Related Compounds 286
12. Compounds with Three-Electron Ligands 286
Titanium, Zirconium, Hafnium 289
Vanadium, Niobium, Tantalum 289
Scandium, Lanthanides, Actinides 289
Chromium, Molybdenum, Tungsten 290
Manganese, Technetium, Rhenium 291
Iron, Ruthenium, Osmium 292
Cobalt, Rhodium, Iridium 294
Nickel, Palladium, Platinum 295
12.2. Cyclopropenyl Complexes 297
12.3. Metal-Carbyne Complexes 299
13. Compounds with Four-Electron Ligands 304
13.1. Butadiene Complexes and Related Compounds 305
13.2. Cyclobutadiene Complexes 308
13.3. η 4-Complexes of Cyclopentadiene, Cyclopentadienone, Fulvene and Heterocycles Derived from Cyclopentadiene 314
Cyclopentadiene 314
Cyclopentadienones 315
Heterocycles 316
Fulvenes 316
13.4. Complexes with Other Cyclic Dienes and Polyenes 317
Cyclohexadiene-1,3 317
Cycloheptadiene-1,3 319
Cycloheptatriene-1,3,5 320
Cyclooctatetrane 320
13.5. Trimethylenemethyl Complexes 321
13.6. Boron-Containing Four-Electron Ligands 322
14. Compounds with Five-Electron Ligands 324
14.1. Transition Metal, η 5-Cyclopentadienyl Complexes 324
Scandium, Yttrium, Lanthanides and Actinides. (Group III Elements) 330
Titanium, Zirconium, Hafnium 331
Vanadium, Niobium, Tantalum 332
Chromium, Molybdenum, Tungsten 334
Manganese, Technetium, Rhenium 336
Iron, Ruthenium, Osmium 337
Cobalt, Rhodium, Iridium 341
Nickel, Palladium, Platinum 343
Copper, Silver, Gold 344
14.2. Acyclic Pentadienyl η 5-Complexes 345
14.3. η 5-Complexes of Some Heterocyclic Ligands 345
14.4. η 5-Cyclohexadienyl Complexes 347
14.5. η 5-Cycloheptadienyl Complexes 348
14.6. Complexes of Carborane Ligands 349
15. Compounds with Six-Electron Ligands 352
15.1. η 6-Complexes of Benzene and its Derivatives 353
Titanium, Zirconium, Hafnium 353
Vanadium, Niobium, Tantalum 354
Chromium, Molybdenum, Tungsten 354
Manganese, Technetium, Rhenium 355
Iron, Ruthenium, Osmium 356
15.2 η 6-Cycloheptatriene Complexes 357
Cobalt, Rhodium, Iridium 357
15.3. Cyclooctatriene and Cyclooctatetraene as Six-Electron Ligands 358
15.4. Some η 6-Complexes with Heterocyclic Ligands 359
16. Compounds with Seven- and Eight-Electron Ligands 362
16.1. Seven-Electron Ligands 362
16.2. Eight-Electron Ligands 364
17. Organometallic Compounds Derived from Acetylenes 366
Titanium, Zirconium, Hafnium 367
17.1. Complexes of Untransformed Acetylenes as Terminal (Dihapto) Ligands 367
Vanadium, Niobium, Tantalum 368
Chromium, Molybdenum, Tungsten 368
Manganese, Technetium, Rhenium 369
Nickel, Palladium, Platinum 369
Iron, Ruthenium, Osmium 369
Cobalt, Rhodium, Iridium 369
17.2. Binuclear Complexes with Bridging Acetylene Ligands 370
17.3. Compounds Incorporating the Acetylene in a Polynuclear Cluster 371
17.4. Complexes Formed by Chemical Transformations of Acetylenes 373
18. Organometallic Compounds with σ -Metal-Carbon Bonds 376
Scandium, Yttrium, Lanthanides and Actinides (Group IIIB Elements) 381
Titanium, Zirconium, Hafnium 382
Chromium, Molybdenum, Tungsten 383
Vanadium, Niobium, Tantalum 383
Manganese, Technetium, Rhenium 385
Iron, Ruthenium, Osmium 386
Cobalt, Rhodium, Iridium 387
Nickel, Palladium, Platinum 388
Copper, Silver, Gold 390
Bibliography 394
Subject Index 506

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Ionel Haiduc: University 'Babes-Bolyai', Cluj-Napoca, Roman

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