Organometallic chemistry and catalysis: with 860 figures and 27 tables
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| Format: | Book |
| Language: | English German |
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Berlin [u.a.]
Springer
2007
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| Series: | Grenoble sciences
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| Subjects: | |
| Online Access: | Inhaltstext Inhaltsverzeichnis |
| Physical Description: | XII, 608 S. graph. Darst. |
| ISBN: | 9783540461289 3540461280 |
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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
PartI
structures of the transition metal complexes
Chapter 1 Monometallic transition metal complexes 23
1. Theligands 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 jr acceptor (CO, C2H4)
and Jt donor ligands (halogeno, alkoxy, amino) 41
6. Molecular orbital diagrams 44
Summary andExercises 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 andExercises 76
vni Organometallic Chemistry and Catalvsis
Part II
The stoichiometric reactions of transition metal complexes
Chapter 3 Redox reactions, oxidative addition and a bond metathesis 81
1. Outer sphere electron transfer 81
2. Inner sphere electron and atom transfer 85
3. Oxidative addition, reductive elimination and o bond metathesis 87
Summary andExercises 106
Chapter 4 Reactions of nucleophiles and electrophiles with complexes 109
1. Nucleophilic reactions 109
2. Reactions of electrophiles 115
Summary andExercises 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 ß alkyl elimination 142
6. a and y 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. Bindingmodes 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
Contents IX
Chapter 8 Metal alkyl and hydride complexes
and other complexes of monohapto X ligands 175
1. Different types of sp* 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 n 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. Jt 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
X Organometaluc Chemistry and Catalysis
Chapter 12 Ionic and polar metal carbon bonds:
alkali and rare earth complexes 289
1. Introduction 289
2. Organometaluc complexes of alkali metals 289
3. Grignard reagents 293
4. The scandium, ytrium, lanthanides and actinides complexes 296
Summary andExercises 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 (B, AI, Ga, In, Tl) 320
5. Group 14 (Si, Ge, Sn, Pb) 328
6. Group 15 (As, Sb, Bi) 340
7. Group 16 (Se, Te) 344
Summary andExercises 346
PartIV
Catalysis
| Introduction to catalysis 351
Chapter 14 Hydrogenation and hydroelementation of alkenes 357
1. Hydrogenation of olefins 357
2. Asymmetrie 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
Contents XI
Chapter 16 Oxidation of olefins 395
1. Historie introduetion 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 andExercises 407
Chapter 17 C H activation and functionalization of alkanes and arenes 409
1. Introduetion 409
2. Alkanes and cycloalkanes 410
3. Aromatics 419
Summary andExercises 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 CO2 transformation 437
Summary and Exercises 438
Chapter 19 Bio organometallic chemistry: enzymatic catalysis 441
1. Introduetion 441
2. Cobalamin: co enzyme vitamin B,2 442
3. Biological redox mediators 445
4. Examples of oxido reduetase enzymes: the mono oxygenases 446
5. Nitrogen fixation by nitrogenase enzyme 448
6. Nickel enzymes 452
Summary andExercises 455
Chapter 20 Heterogeneous catalysis 457
1. Introduetion 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
XII Organometallic Chemistry and Catalysis
PartV
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 |
| adam_txt |
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
PartI
structures of the transition metal complexes
Chapter 1 Monometallic transition metal complexes 23
1. Theligands 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 jr acceptor (CO, C2H4)
and Jt donor ligands (halogeno, alkoxy, amino) 41
6. Molecular orbital diagrams 44
Summary andExercises 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 andExercises 76
vni Organometallic Chemistry and Catalvsis
Part II
The stoichiometric reactions of transition metal complexes
Chapter 3 Redox reactions, oxidative addition and a bond metathesis 81
1. Outer sphere electron transfer 81
2. Inner sphere electron and atom transfer 85
3. Oxidative addition, reductive elimination and o bond metathesis 87
Summary andExercises 106
Chapter 4 Reactions of nucleophiles and electrophiles with complexes 109
1. Nucleophilic reactions 109
2. Reactions of electrophiles 115
Summary andExercises 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 ß alkyl elimination 142
6. a and y 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. Bindingmodes 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
Contents IX
Chapter 8 Metal alkyl and hydride complexes
and other complexes of monohapto X ligands 175
1. Different types of sp* 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 n 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. Jt 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
X Organometaluc Chemistry and Catalysis
Chapter 12 Ionic and polar metal carbon bonds:
alkali and rare earth complexes 289
1. Introduction 289
2. Organometaluc complexes of alkali metals 289
3. Grignard reagents 293
4. The scandium, ytrium, lanthanides and actinides complexes 296
Summary andExercises 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 (B, AI, Ga, In, Tl) 320
5. Group 14 (Si, Ge, Sn, Pb) 328
6. Group 15 (As, Sb, Bi) 340
7. Group 16 (Se, Te) 344
Summary andExercises 346
PartIV
Catalysis
| Introduction to catalysis 351
Chapter 14 Hydrogenation and hydroelementation of alkenes 357
1. Hydrogenation of olefins 357
2. Asymmetrie 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
Contents XI
Chapter 16 Oxidation of olefins 395
1. Historie introduetion 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 andExercises 407
Chapter 17 C H activation and functionalization of alkanes and arenes 409
1. Introduetion 409
2. Alkanes and cycloalkanes 410
3. Aromatics 419
Summary andExercises 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 CO2 transformation 437
Summary and Exercises 438
Chapter 19 Bio organometallic chemistry: enzymatic catalysis 441
1. Introduetion 441
2. Cobalamin: co enzyme vitamin B,2 442
3. Biological redox mediators 445
4. Examples of oxido reduetase enzymes: the mono oxygenases 446
5. Nitrogen fixation by nitrogenase enzyme 448
6. Nickel enzymes 452
Summary andExercises 455
Chapter 20 Heterogeneous catalysis 457
1. Introduetion 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
XII Organometallic Chemistry and Catalysis
PartV
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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| dewey-full | 547.05 |
| dewey-hundreds | 500 - Natural sciences and mathematics |
| dewey-ones | 547 - Organic chemistry |
| dewey-raw | 547.05 |
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| id | DE-604.BV022395505 |
| illustrated | Illustrated |
| index_date | 2024-07-02T17:16:24Z |
| indexdate | 2024-07-20T09:15:27Z |
| institution | BVB |
| isbn | 9783540461289 3540461280 |
| language | English German |
| oai_aleph_id | oai:aleph.bib-bvb.de:BVB01-015604251 |
| oclc_num | 633417655 |
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| owner_facet | DE-91G DE-BY-TUM DE-19 DE-BY-UBM DE-703 DE-634 DE-11 |
| physical | XII, 608 S. graph. Darst. |
| publishDate | 2007 |
| publishDateSearch | 2007 |
| publishDateSort | 2007 |
| publisher | Springer |
| record_format | marc |
| series2 | Grenoble sciences |
| spelling | Astruc, Didier Verfasser (DE-588)112945058 aut Chimie organométallique Organometallic chemistry and catalysis with 860 figures and 27 tables Didier Astruc Berlin [u.a.] Springer 2007 XII, 608 S. graph. Darst. txt rdacontent n rdamedia nc rdacarrier Grenoble sciences Katalyse (DE-588)4029921-1 gnd rswk-swf Metallorganische Verbindungen (DE-588)4038906-6 gnd rswk-swf Metallorganische Verbindungen (DE-588)4038906-6 s Katalyse (DE-588)4029921-1 s DE-604 text/html http://deposit.dnb.de/cgi-bin/dokserv?id=2853640&prov=M&dok_var=1&dok_ext=htm Inhaltstext HBZ Datenaustausch application/pdf http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=015604251&sequence=000002&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA Inhaltsverzeichnis |
| spellingShingle | Astruc, Didier Organometallic chemistry and catalysis with 860 figures and 27 tables Katalyse (DE-588)4029921-1 gnd Metallorganische Verbindungen (DE-588)4038906-6 gnd |
| subject_GND | (DE-588)4029921-1 (DE-588)4038906-6 |
| title | Organometallic chemistry and catalysis with 860 figures and 27 tables |
| title_alt | Chimie organométallique |
| title_auth | Organometallic chemistry and catalysis with 860 figures and 27 tables |
| title_exact_search | Organometallic chemistry and catalysis with 860 figures and 27 tables |
| title_exact_search_txtP | Organometallic chemistry and catalysis with 860 figures and 27 tables |
| title_full | Organometallic chemistry and catalysis with 860 figures and 27 tables Didier Astruc |
| title_fullStr | Organometallic chemistry and catalysis with 860 figures and 27 tables Didier Astruc |
| title_full_unstemmed | Organometallic chemistry and catalysis with 860 figures and 27 tables Didier Astruc |
| title_short | Organometallic chemistry and catalysis |
| title_sort | organometallic chemistry and catalysis with 860 figures and 27 tables |
| title_sub | with 860 figures and 27 tables |
| topic | Katalyse (DE-588)4029921-1 gnd Metallorganische Verbindungen (DE-588)4038906-6 gnd |
| topic_facet | Katalyse Metallorganische Verbindungen |
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