Astruc D. Organometallic chemistry and catalysis (Berlin; Heidelberg, 2007). - ОГЛАВЛЕНИЕ / CONTENTS
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ОбложкаAstruc D. Organometallic chemistry and catalysis. - Berlin; Heidelberg: Springer, 2007. - xii, 608 p.: ill. - (Grenoble sciences). - Ref.: p.553-589. - Ind.: p.595-608. - ISBN 978-3-540-46128-9
 

Оглавление / Contents
 
Introduction .................................................... 1
1  Organization of the text ..................................... 1
2  Frontiers of organometallic chemistry ........................ 2
3  Situation of the book with respect to teaching ............... 2
4  Reference books and other selected references ................ 3

History of organometallic chemistry ............................. 5
1760-1900: The first complexes .................................. 5
1900-1950: Grignard, Sabatier, and catalysis in Germany ......... 6
1950-1960: The discovery of ferrocene and the boom of 
organometallic chemistry ........................................ 7
1961-1981: The discovery of multiple metal-carbon bonds
and the golden age of catalysis ................................. 9
1970-1985: Activation of C-H bonds in hydrocarbons, a-bond
metathesis and H2 as a ligand .................................. 16
Current trends ................................................. 18

Part I
Structures of the transition-metal complexes 

Chapter 1 - Monometallic transition-metal complexes ............ 23
1  The ligands ................................................. 23
2  The characteristics of the transition-metal in the 
   complexes ................................................... 32
3  Hapticity of the ligands and linear writing of the complex
   formulas .................................................... 36
4  The "18-electron rule": tendencies and exceptions ........... 37
5  Bonding between the transition metal and the л-acceptor
   (CO, C2H4) and π-donor ligands (halogeno, alkoxy, amino) .... 41
6  Molecular orbital diagrams .................................. 44
Summary and Exercises .......................................... 45

Chapter 2 - Bimetallic transition-metal complexes and 
clusters ....................................................... 47
1  The metal-metal bond in bimetallic complexes ................ 48
   Types of molecular magnetism ................................ 59
2  Clusters .................................................... 60
3  The isolobal analogy ........................................ 73
Summary and Exercises .......................................... 76

Part II
The stoichiometric reactions of transition-metal complexes

Chapter 3 - Redox reactions, oxidative addition and σ-bond
metathesis ..................................................... 81
1  Outer-sphere electron transfer .............................. 81
2  Inner-sphere electron- and atom transfer .................... 85
3  Oxidative addition, reductive elimination and σ-bond
   metathesis .................................................. 87
Summary and Exercises ......................................... 106

Chapter 4 - Reactions of nucleophiles and electrophiles with
            complexes ......................................... 109
1  Nucleophilic reactions ..................................... 109
2  Reactions of electrophiles ................................. 115
Summary and Exercises ......................................... 119

Chapter 5 - Ligand substitution reactions ..................... 121
1  Introduction ............................................... 121
2  "Pairwise" mechanisms ...................................... 121
3  Electron-transfer-chain and atom-transfer-chain
   mechanisms ................................................. 127
4  Substitution of XLn ligands (n = 0-2) ...................... 132
Summary and Exercises ......................................... 133

Chapter 6 - Insertion and extrusion reactions ................. 135
1  Introduction ............................................... 135
2  CO 1,1 migratory insertion ................................. 136
3  Methylene insertion and extrusion .......................... 139
4  1,2 migratory insertion of alkenes and alkynes into M-H 
   bonds ...................................................... 140
5  Insertion of alkenes into metal-alkyl bonds and the
   reverse reaction: C-C activation by β-alkyl elimination .... 142
6  α and γ-elimination ........................................ 143
Summary and Exercises ......................................... 146

Part III
The main families of organometallic complexes

Chapter 7 - Metal carbonyls and complexes of other monohapto
L ligands ..................................................... 151
1  Introduction ............................................... 151
2  Syntheses .................................................. 152
3  Binding modes .............................................. 153
4  Reactions .................................................. 159
5  Ligands isoelectronic to CO: CNR, CS, CSe, N2 and NO+ ...... 162
6  DioxygenO2 ................................................. 168
7  Phosphanes ................................................. 168
8  Weak L ligands and their role to generate organometallic
   Lewis acids ................................................ 171
Summary and Exercises ......................................... 172

Cluster 8 - Metal-alkyl and -hydride complexes and other 
complexes of monohapto X ligands .............................. 175
1  Different types of sp3 metal-carbon bonds .................. 175
2  Stability of metal-alkyl complexes ......................... 175
3  Synthesis of metal-alkyl complexes ......................... 179
4  Properties of metal-alkyl complexes ........................ 180
5  Metallocycles .............................................. 181
6  Metal-aryl, -vinyl, -alkynyl, -silyl, and -stannyl 
   complexes .................................................. 182
7  Metal-hydrides and the dihydrogen ligand ................... 184
8  Alkoxy and amido complexes ................................. 193
Summary and Exercises ......................................... 194

Chapter 9 - Metal-carbene and -carbyne complexes and 
multiple bonds with transition metals ......................... 197
1  Metal-carbene complexes .................................... 197
2  Metal-carbyne complexes .................................... 215
3  Multiple bond between a heteroatom and a transition 
   metal: oxo, imido, phosphinidene and nitrido ligands ....... 217
Summary and Exercises ......................................... 223

Chapter 10 - π complexes of mono- and polyenes and enyls ...... 225
1  Metal-olefin complexes ..................................... 225
2  Metal-diene complexes and analogues ........................ 228
3  Metal-alkyne complexes ..................................... 231
4  π-Allyl complexes ......................................... 233
5  Polyenyl complexes ......................................... 237
6  Arene complexes ............................................ 242
Summary and Exercises ......................................... 248

Chapter 11 - Metallocenes and sandwich complexes .............. 251
1  Structure of the metallocenes .............................. 251
2  Redox properties of the sandwich metallocenes .............. 255
3  Metallocene synthesis ...................................... 256
4  Chemical properties of metallocenes ........................ 258
5  Triple- and multiple-decker sandwich complexes ............. 266
6  Non-sandwich metallocenes derivatives ...................... 268
7  Metal-bis-arene sandwich complexes ......................... 270
8  Cylopentadienyl-metal-arene complexes ...................... 274
Summary and Exercises ......................................... 287

Chapter 12 - Ionic and polar metal-carbon bonds: alkali and
rare-earth complexes .......................................... 289
1  Introduction ............................................... 289
2  Organometallic complexes of alkali metals .................. 289
3  Grignard reagents .......................................... 293
4  The scandium, ytrium, lanthanides and actinides complexes .. 296
Summary and Exercises ......................................... 310

Chapter 13 - Covalent chemistry of the organoelements
of frontier (11,12) and main (13-16) groups ................... 313
1  Introduction ............................................... 313
2  Group 11 (Cu, Ag, Au) ...................................... 314
3  Group 12 (Zn, Cd, Hg) ...................................... 316
4  Group 13 (В, AI, Ga, In, Tl) ............................... 320
5  Group 14 (Si, Ge, Sn, Pb) .................................. 328
6  Group 15 (As, Sb, Bi) ...................................... 340
7  Group 16 (Se, Те) .......................................... 344
Summary and Exercises ......................................... 346

Part IV Catalysis

Introduction to catalysis ..................................... 351

Chapter 14 - Hydrogenation and hydroelementation of alkenes ... 357
1  Hydrogenation of olefins ................................... 357
2  Asymmetric hydrogenation ................................... 360
4  Hydroboration of olefins ................................... 362
5  Hydrocyanation of olefins .................................. 362
6  Hydroamination of olefins and alkynes ...................... 363
Summary and Exercises ......................................... 364

Chapter 15 - Transformations of alkenes and alkynes ........... 367
1  Ziegler-Natta-type olefin polymerization ................... 367
2  Metathesis of alkenes, alkynes and cycloalkenes ............ 373
3  Olefin dimerization and oligomerization .................... 386
4  Olefin isomerization ....................................... 390
Summary and Exercises ......................................... 392

Chapter 16 - Oxidation of olefins ............................. 395
1  Historic introduction and radical-type oxidation ........... 395
2  Ethylene oxidation to acetaldehyde: Wacker process ......... 396
4  Epoxidation of olefins ..................................... 399
5  Hydroxylation by metal-oxo complexes ....................... 402
6  Phase-transfer catalysis in oxidation chemistry ............ 405
Summary and Exercises ......................................... 407

Chapter 17 - C-H activation and functionalization of 
alkanes and arenes ............................................ 409
1  Introduction ............................................... 409
2  Alkanes and cycloalkanes ................................... 410
3  Aromatics .................................................. 419
Summary and Exercises ......................................... 428

Chapter 18 - Carbonylation and carboxylation reactions ........ 431
1  Carbonylation of methanol: Monsanto process ................ 431
2  Olefin hydroformylation: oxo process ....................... 433
3  Carbonylation of alkenes and alkynes in the presence of
   a nucleophile: the Reppe reaction .......................... 434
4  Carbonylation of aryl halides in the presence of a
   nucleophile ................................................ 436
5  Catalysis of СO2 transformation ............................ 437
Summary and Exercises ......................................... 438

Chapter 19 - Bio-organometallic chemistry: enzymatic 
catalysis ..................................................... 441
1  Introduction ............................................... 441
2  Cobalamin: co-enzyme vitamin B12 ........................... 442
3  Biological redox mediators ................................. 445
4  Examples of oxido-reductase enzymes: the mono-oxygenases ... 446
5  Nitrogen fixation by nitrogenase enzyme .................... 448
6  Nickel enzymes ............................................. 452
Summary and Exercises ......................................... 455

Chapter 20 Heterogeneous catalysis ............................ 457
1  Introduction ............................................... 457
2  Concepts of heterogeneous catalysis ........................ 460
3  CO and CO2 hydrogenation and Fischer-Tropsch chemistry ..... 469
4  Transformation of hydrocarbons ............................. 475
5  Metathesis of alkanes, alkenes and alkynes ................. 477
6  Oxidation of hydrocarbons .................................. 480
7  Nanoparticle catalysis: the fast growing frontier between 
   homogeneous and heterogeneous catalysis .................... 483
Summary and Exercises ......................................... 485

Part V
Applications in organic synthesis

Chapter 21 - Organometallic complexes in organic synthesis
Examples of applications ...................................... 489
1  Protection and stabilization of unsaturated organic
   derivatives and fragments .................................. 489
2  Nucleophilic and electrophilic reactions on hydrocarbon 
   ligands .................................................... 492
3  General methods of C-C bond formation using the oxidative
   addition of an organic halide or a related electrophile .... 497
4  Extension of palladium catalysis to the formation of C-O
   and C-N bonds .............................................. 516
5  Oxidative coupling reactions of alkynes with other
   unsaturated fragments for the formation of cyclic and
   heterocyclic compounds ..................................... 518
6  Metal-carbene complexes in organic synthesis ............... 521
7  Examples of asymmetric catalysis ........................... 523
   Summary and Exercises ...................................... 530
Answers to exercises .......................................... 535
References .................................................... 553
Abbreviations ................................................. 591
Index ......................................................... 595
Atomic weights of the elements ................................ 609
Periodic table of the elements ................................ 611


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