Organometallics and catalysis: an introduction
Gespeichert in:
| 1. Verfasser: | |
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| Format: | Buch |
| Sprache: | English |
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Oxford
Oxford University Press
[2015]
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| Online-Zugang: | Klappentext Inhaltsverzeichnis |
| Beschreibung: | xviii, 410 Seiten Illustrationen |
| ISBN: | 9780199668212 |
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| 100 | 1 | |a Bochmann, Manfred |e Verfasser |0 (DE-588)106871994X |4 aut | |
| 245 | 1 | 0 | |a Organometallics and catalysis |b an introduction |c Manfred Bochmann, University of East Anglia |
| 264 | 1 | |a Oxford |b Oxford University Press |c [2015] | |
| 264 | 4 | |c © 2015 | |
| 300 | |a xviii, 410 Seiten |b Illustrationen | ||
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Datensatz im Suchindex
| _version_ | 1804152697445679104 |
|---|---|
| adam_text | Teachers and students of organometallic chemistry will find this superb book to be an
indispensable resource Dr Richard Lay field, The University of Manchester
This is essential reading for advanced undergraduates and postgraduate research students
working in, or at the borders of, contemporary organometallic chemistry and catalysis
Professor Philip Mountford, University of Oxford
I believe this book will become the new standard text for teaching organometallic
chemistry at the undergraduate and graduate levels Professor Douglas W Stephan, University of Toronto
The most student-friendly overview of the essential
concepts of
ill
Striking just the right balance between breadth and depth
—and with features throughout to support the learning
process—Organometallics and Catalysis: An introduction is
the perfect introduction for undergraduate and graduate
students who need a thorough grounding in the subject or
are embarking on new research areas.
The book is enriched throughout with examples that demon-
strate how our understanding of organometallic chemistry
has led to new applications in research and industry—not
least in relation to catalysis—and extensive reaction schemes
and structures give added clarity to the concepts being
explained.
Written by an experienced educator, researcher
and author to provide a uniformly authoritative yet
easy-to-digest resource
The coverage is guided by the requirements of typical
university teaching courses, without excessive detail.
Topical applications highlight the importance and
consequences of fundamental material
Pictures say more than a thousand words: numerous
illustrations help students to visualise even the most
challenging of concepts
Key points and questions dispersed throughout the text
help to reinforce understanding and make it an effective
learning tool.
*
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M A N F; E [) B0C HA is Professor
of Inorganic Chemistry at the School of Chemistry,
University of East Anglia, Norwich, UK.
Detailed ContentSj,
Preface v
General Information viii
Ligand Nomenclature x
1. Organometallic Compounds of Main Group Elements l
1.1 General and BondingConsiderations 2
Box 1.1 Lithium ion intercalation 7
Key points 7
Exercises 7
1.2 Alkali Metal Organometallics: Lithium 8
1.2.1 Synthesis 8
1.2.2 Structure of Lithium Alkyls 10
1.2.3 Reactivity of Lithium Alkyls 11
1.2.4 Organometallic Compounds of the Heavier Alkali Metals: Na-Cs 15
Box 1.2.4 Mixed-metal complexes and superbases 17
Key points 16
Exercises 16
1.3 Organometallic Compounds of Alkaline Earth Metals 18
1.3.1 Beryllium 18
1.3.2 Magnesium 18
1.3.2.1 Synthesis 18
1.3.2.2 Structures of Magnesium Reagents 23
1.3.2.3 Reactions of Magnesium Reagents 24
Box 1.3.2 Grignard reagents 19
1.3.3 Calcium, Strontium, and Barium 23
Box 1.3.3 Unusual Ca(l) compound 27
Key points 27
Exercises 27
1.4 Zinc, Cadmium, and Mercury 28
1.4.1 Zinc Compounds 28
Box 1.4.1. Zinc alkyl purification 29
1.4.2 Cadmium Compounds 32
1.4.3 Mercury Compounds 33
1.4.3.1 Synthesis 33
1.4.3.2 Structural Aspects 35
Box 1.4.3 Organomercury compounds in vivo 36
Key points 37
Exercises 37
xii
DETAILED CONTENTS
1.5 Organometallic Compounds of the Boron Group 38
1.5.1 Boron Compounds 38
1.5.1.1 Synthetic Methods A3
1.5.1.2 Reactivity of Boron Compounds 44
1.5.1.3 Structure and Bonding 44
Box 1.5.1.1 The importance of sterîc factors: stabilization
of a transition state 42
Boxl.5.1.2 Boron in uncommon bonding situations 45
Box 1.5.1.3 Determination of Lewis acidity 45
Box 1.5.1.4 Substituent effects in boranes: C6F5 versus C6H5 46
1.5.2 Aluminium 46
1.5.2.1 Synthesis 46
1.5.2.2 Structures and Properties 48
Box 1.5.2.1 27Al NMR spectroscopy 49
Box 1.5.2.2 Low-coordinate organoaluminium cations 50
1.5.2.3 Reactivity 51
Box 1.5.2.3 The structure and function of MAO 53
1.5.2.4 Aluminium Compounds in Low Oxidation States 54
1.5.3 Gallium, Indium, and Thallium 55
1.5.3.1 Compounds in the Oxidation State III 56
1.5.3.2 Ga, In, Tl Compounds in Low Oxidation States 58
Box 1.5.3.1 Low-valent metal alkyls and aryls 60
Box 1.5.3.2 Metal alkyls as semiconductor precursors 62
Key points 63
Exercises 63
1.6 Organometallic Compounds of the Carbon Group 64
1.6.1 Silicon Compounds 64
1.6.1.1 Synthetic Methods 64
1.6.1.2 Reactivity 65
Box 1.6.1.2 Silicone polymers 66
1.6.1.3 Compounds of Low-Valent Si 68
Box 1.6.1.3 29Si NMR Spectroscopy 71
1.6.2 Germanium 71
1.6.3 Tin Compounds 71
Box 1.6.3 Toxicity of tin(IV) reagents 72
1.6.3.1 Synthesis of Tin Compounds 72
1.6.3.2 Structures of Sn(IV) Compounds 73
1.6.3.3 Reactivity of Tin Compounds 74
1.6.3.4 Tin in Oxidation States +lli and +11: Sn-Sn Bonds,
Tin Radicals, and Stannylenes 77
Box 1.6.3.1 Tin(ll) and lone electron pairs 78
Box 1.6.3.2 119Sn NMR spectroscopy 78
1.6.4 Lead Compounds 79
Key points 80
Exercises 80
DETAILED CONTENTS
OrganometaUîc Compounds of Transition Metals 81
Box 2.0 Electron configuration and d-electron count 82
2.1 Ligand Types 84
2.2 Common Types of OrganometaUîc Complexes 86
2.3 Electron Countingand the 16/18-Electron Rule 91
2.3.1 Counting Conventions 91
2.3.2 Electron Countingand Oxidation States 92
Key points 95
Exercises 95
2.4 Ligand Properties and Metal-Ligand Bonding 96
2.4.1 Carbon Monoxide 96
Box 2.4.1 CO reactivity 99
2.4.2 Alkene and Alkyne Ligands 98
Box 2.4.2 13C NMR spectroscopy 101
2.4.3 n-Donor Ligands 101
2.4.4 Phosphines, Carbenes: Electronic and Steric Parameters 102
2.4.5 Common Co-Ligands 107
Key points 109
Exercises 109
2.5 L-Type rr-Acceptor Ligands: Metal Carbonyl Complexes 110
2.5.1 Synthesis of Metal Carbonyls 110
Box 2.5.1 Metal carbonyl complexes in biology
and medicine 112
2.5.2 Bondingin BinuclearandClusterComplexes 113
Key points 118
Exercises 118
2.5.3 Reaction Mechanisms of Metal Carbonyls 118
2.5.3.1 Ligand Substitution: Principles and Mechanisms 118
2.5.3.2 CO Ligand Substitution: Overview and Methods 122
2.5.3.3 Nucleophilic Attack on CO 124
Box 2.5.3 Nucleophilic attack on CO for hydrogen
production 125
2.5.4 Metal Carbonyl Anions 125
2.5.5 Metal Carbonyl Cations 128
2.5.6 Metal Carbonyl Halides 129
2.5.7 Metal Carbonyl Hydrides 130
2.5.7.1 Syntheses 130
2.5.7.2 Reactions 132
Box 2.5.7 CO reduction: the Fischer-Tropsch process 134
2.5.8 Related n֊Acceptor Ligands 134
2.5.8.1 CS, CSe, and CTe 134
2.5.8.2 Isocyanide Complexes 135
2.5.8.3 Nitrosyl Complexes 136
Key points 137
Exercises 137
xiv
DETAILED CONTENTS
2.6 L-Type n-Acceptor Ligands: Alkenes, Dienes, and Alkynes 139
2.6.1 Alkene Complexes 141
2.6.1.1 Synthesis of Alkene Complexes 141
2.6.1.2 Reactions of Alkene Complexes 145
2.6.2 Diene Complexes 150
2.6.2.1 Synthesis of Conjugated Diene Complexes 150
2.6.2.2 Bondingin Complexes of Conjugated Dienes 151
Box 2.6.2.2 Molecular wires and switches 154
2.6.2.3 Reactions of Conjugated Diene Complexes 153
Box 2.6.2.3 Nucleophilic attack on n-ligands:
the Davies-Green-Mingos rules 157
2.6.3 Alkyne Complexes 158
2.6.3.1 Synthesis of Alkyne Complexes 160
2.6.3.2 Reactivity of Alkyne Complexes 161
Box 2.6.3 Alkyne complexes in organic synthetic
methodology 165
Key points 168
Exercises 168
2.7 LX- and L2X-Type n-Ligands: Allyl and Enyl Complexes 169
2.7.1 Metal Allyl Complexes 169
2.7.1.1 Synthesis 169
2.7.1.2 Properties 171
2.7.1.3 Reactivity of Allyl Complexes 172
Box 2.7.1.3 Metal allyl catalysts 175
2.7.2 Metal Dienyl and Trienyl Complexes 177
2.7.2.1 Synthesis 177
2.7.2.2 Reactivity 178
Box 2.7.2.2 Metal dienyl complexes in organic synthesis 178
Key points 179
Exercises 179
2.8 L2X֊Type n-Acceptor Ligands: Metallocene Complexes 180
2.8.1 Bis(cyclopentadienyl) Complexes 180
2.8.1.1 Synthesis of Metallocene Complexes 185
2.8.1.2 Structure and Bonding in MCp2 Complexes 185
2.8.1.3 Reactions of MCp2 Complexes 188
Box 2.8.1.3 Ferrocenes in medicine and catalysis 191
2.8.2 Bent Metallocene Complexes 1^4
2.8.2.1 Synthesis of Bent Sandwich Complexes 194
2.8.2.2 Structures of Bent Metallocene Complexes 196
2.8.2.3 Reactivity of Bent Metallocene Complexes 198
Box 2,8.2.1 Structural aspect of electrophilic metallocenes: square-
planarand trigonal-bipyramidal C 201
Box 2.8.2.2 Metallocene materials: single-molecule
magnets (SMMs)
Key points ^4
Exercises ^4
DETAILED CONTENTS
2.8.3 Mono-Cyclopentadienyl (Half-Sandwich) Complexes 204
2.8.3.1 Synthesis of Mono-Cp Complexes 205
2.8.3.2 Reactivity of Mono-Cp Complexes 207
Box 2.8.3 Half-sandwich complexes in stereoselective
synthesis 209
Key points 211
Exercises 211
2.9 Arene Complexes 212
2.9.1 Bis(Arene) Sandwich Complexes 212
2.9.1.1 Synthesis and Structures 212
2.9.1.2 Reactivity of Bis(Arene) Complexes 214
2.9.2 Arene Half-Sandwich Complexes 215
2.9.2.1 Synthesis and Structures of Mono-Arene Complexes 216
Box 2.9.2.1 Mono-arene complexes for cancertreatment 217
2.9.2.2 Reactivity of Mono-Arene Carbonyl Complexes 218
2.9.3 Arene Complexes with Less Common Coordination Modes 221
2.9.4 Larger Arene Ligands: 7-, 8-and 9-Membered Rings 222
2.9.4.1 n-C7H7 Complexes 222
2.9.4.2 tt-C8H8 Complexes 223
2.9.4.3 n-C9H9 Complexes 225
2.9.4.4 n-Complexes of Heterocycles 225
Key points 227
Exercises 227
2.10 Sigma Complexes 228
2.10.1 H2 Complexes 228
2.10.2 Alkane and Silane complexes 229
Box 2.10.2 Alkane dehydrogenation and functionalization 232
Key points 234
2.11 Complexes with M-Ca-Bonds 235
2.11.1 Energetics and Reactivity of Metal Alkyls 235
2.11.2 Types and Bonding Modes of M-C o-Bonded Ligands 237
2.11.2.1 M-R Ligand Types 237
2.11.2.2 M-R Bonding Modes 238
2.11.2.3 The Importance of Steric Hindrance 240
2.11.3 Synthesis of Metal Alkyls 242
2.11.3.1 Synthesis of Homoleptic Metal Alkyl Complexes 242
Box 2.11.3.1 The structures of homoleptic metal methyl
complexes 245
2.11.3.2 Synthesis of Heteroleptic Metal Alkyl Complexes 245
Box 2.11.3.2 Synthetic examples 252
2.11.3.3 Alkynyl Complexes 256
2.11.4 Reactivity of Metal Alkyls 257
2.11.4.1 M-C Bond Protonolysis 258
2.11.4.2 Cleavage by Halogens 259
2.11.4.3 Chalcogen Insertions 259
2.11.4.4 Cleavage by Lewis Acids 260
XVI
DETAILED CONTENTS
2.11.4.5 Cleavage by Oxidation 260
2.11.4.6 Hydrogenolysis of M~C Bonds 261
2.11.4.7 Insertion of Electrophilic Heterocumulenes 261
Box 2.11.4.7 C02 utilization in synthesis 262
2.11.4.8 Insertion of NO 263
2.11.4.9 Insertion of CO 263
2.11.4.10 Insertion of Isocyanides 267
2.11.4.11 Insertion of Alkenes 268
2.11.4.12 Insertion of Alkynes 270
2.11.4.13 Reactions of Metal Alkyls with Non-Innocent Ligands 271
Box 2.11.4.12 Transition metal alkyl complexes in vivo 272
Key points 274
Exercises 274
2.12 Alkylidene Complexes 275
Box 2.12 NMR spectroscopy of metal carbenes 276
2.12.1 Synthesis of Alkylidene Complexes 276
2.12.1.1 Synthesis of Alkylidene Complexes in Low Oxidation States:
FischerCarbenes 276
2.12.1.2 Synthesis of Alkylidene Complexes in High Oxidation States (d°) 279
2.12.1.3 Vinylidene Complexes 281
Box 2.12.1.2 Alkynyl-allenylidene rearrangements 282
2.12.2 Reactivity of Alkylidene Complexes 282
2.12.2.1 Reactions of FischerCarbenes 282
Box 2.12.2.1 The Dötz reaction 284
2.12.2.2 Reactions of d° Alkylidene Complexes 283
2.12.2.3 Ruthenium Carbene Complexes 288
Box 2.12.2.3 Applications of Olefin Metathesis 289
Key points 292
Exercises 292
2.13 Complexes with M=C Triple Bonds: Carbynes 293
2.13.1 Synthesis of Carbyne Complexes 293
2.13.2 Reactions of Carbyne Complexes 295
2.13.3 Bridging Carbene and Carbyne Complexes 296
Key points 297
Exercises 297
3. Homogeneous Catalysis with Organometallic Transition Metal Complexes 299
3.1 General Considerations 301
3.2 Key Reaction Steps in Homogeneous Catalysis 304
3.2.1 Catalyst Activation 304
3.2.2 Oxidative Addition 305
3.2.3 Reductive Elimination 307
3.2.4 Nucleophilic Attack on Coordinated Substrates 309
Key points 309
Exercises 310
DETAILED CONTENTS
XVÜ
3.3 Catalytic H-H and H-X Additions
3.3.1 Hydrogenation
3.3.1.1 General Hydrogenation Catalysis
3.3.1.2 Arene Hydrogenation
3.3.1.3 Asymmetric Hydrogenation
Box3.3.1.3 Applications of asymmetric hydrogenations
3.3.1.4 Transfer Hydrogenation
Box 3.3.1.A Hydrogen storage molecules and H2 release
3.3.1.5 Outer-Sphere Hydrogenation of Ketones
3.3.2 Hydrosilylation
3.3.3 Isomerizations
3.3.4 Hydrocyanation
Box 3.3.4 Applications of asymmetric hydrocyanation
3.3.5 Hydroamination
Key points
Exercises
3.4 Catalytic Carbonylations
3.4.1 Hydroformylation
3.4.2 Carbonylation Reactions
3.4.2.1 Alcohol Carbonylations
3.4.2.2 Alkene and Alkyne Carbonylations
Key points
Exercises
3.5 Alkene Oxidations
Key points
3.6 Coupling Reactions
3.6.1 C-C Cross-Coupling Reactions
3.6.2 C-N Cross-Coupling Reactions
3.6.3 Coupling Reactions with Carbonylation
3.6.4 Heck Arylations
Box 3.6.4 Mechanistic aspects of the Heck reaction
Key points
Exercises
3.7 Alkene Polymerizations
3.7.1 Ziegler Catalysts
3.7.1.1 Catalyst Composition
Box 3.7.1.1 Polymers and polymer structure
3.7.1.2 Mechanism of Ziegler Catalysts
3.7.2 Metal Complexes as Polymerization Catalysts
3.7.2.1 Catalyst Activation and Active Species
3.7.2.2 Alkene Polymerization Reactions
3.7.2.3 Stereoselective Polymerization
Box 3.7.2.3 Chain-shuttling polymerization
3.7.3 Alkene Oligomerizations
Key points
Exercises
311
311
311
314
315
319
321
322
322
323
324
325
328
329
330
331
332
332
334
334
336
339
340
341
342
343
344
345
345
346
346
347
347
349
349
349
350
353
355
356
359
362
365
366
368
368
DETAILED CONTENTS
Appendix 1
Appendix 2
Appendix 3
Appendix 4
Index
Commonly Used Solvents and Their Properties
Number and Symmetry of Infrared-Active Vibrations of Metal
Carbonyl Complexes
Answers to Exercises
Further Reading
|
| any_adam_object | 1 |
| author | Bochmann, Manfred |
| author_GND | (DE-588)106871994X |
| author_facet | Bochmann, Manfred |
| author_role | aut |
| author_sort | Bochmann, Manfred |
| author_variant | m b mb |
| building | Verbundindex |
| bvnumber | BV042185845 |
| classification_rvk | VH 9700 VH 9701 VK 5560 |
| ctrlnum | (OCoLC)903081787 (DE-599)BVBBV042185845 |
| discipline | Chemie / Pharmazie |
| format | Book |
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| genre | Einführung gnd |
| genre_facet | Einführung |
| id | DE-604.BV042185845 |
| illustrated | Illustrated |
| indexdate | 2024-07-10T01:14:50Z |
| institution | BVB |
| isbn | 9780199668212 |
| language | English |
| oai_aleph_id | oai:aleph.bib-bvb.de:BVB01-027624990 |
| oclc_num | 903081787 |
| open_access_boolean | |
| owner | DE-188 DE-703 DE-355 DE-BY-UBR DE-29T DE-11 DE-19 DE-BY-UBM |
| owner_facet | DE-188 DE-703 DE-355 DE-BY-UBR DE-29T DE-11 DE-19 DE-BY-UBM |
| physical | xviii, 410 Seiten Illustrationen |
| publishDate | 2015 |
| publishDateSearch | 2015 |
| publishDateSort | 2015 |
| publisher | Oxford University Press |
| record_format | marc |
| spelling | Bochmann, Manfred Verfasser (DE-588)106871994X aut Organometallics and catalysis an introduction Manfred Bochmann, University of East Anglia Oxford Oxford University Press [2015] © 2015 xviii, 410 Seiten Illustrationen txt rdacontent n rdamedia nc rdacarrier Metallorganische Verbindungen (DE-588)4038906-6 gnd rswk-swf Katalyse (DE-588)4029921-1 gnd rswk-swf Einführung gnd rswk-swf Metallorganische Verbindungen (DE-588)4038906-6 s Katalyse (DE-588)4029921-1 s Einführung f DE-604 Digitalisierung UB Bayreuth - ADAM Catalogue Enrichment application/pdf http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=027624990&sequence=000003&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA Klappentext Digitalisierung UB Bayreuth - ADAM Catalogue Enrichment application/pdf http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=027624990&sequence=000004&line_number=0002&func_code=DB_RECORDS&service_type=MEDIA Inhaltsverzeichnis |
| spellingShingle | Bochmann, Manfred Organometallics and catalysis an introduction Metallorganische Verbindungen (DE-588)4038906-6 gnd Katalyse (DE-588)4029921-1 gnd |
| subject_GND | (DE-588)4038906-6 (DE-588)4029921-1 |
| title | Organometallics and catalysis an introduction |
| title_auth | Organometallics and catalysis an introduction |
| title_exact_search | Organometallics and catalysis an introduction |
| title_full | Organometallics and catalysis an introduction Manfred Bochmann, University of East Anglia |
| title_fullStr | Organometallics and catalysis an introduction Manfred Bochmann, University of East Anglia |
| title_full_unstemmed | Organometallics and catalysis an introduction Manfred Bochmann, University of East Anglia |
| title_short | Organometallics and catalysis |
| title_sort | organometallics and catalysis an introduction |
| title_sub | an introduction |
| topic | Metallorganische Verbindungen (DE-588)4038906-6 gnd Katalyse (DE-588)4029921-1 gnd |
| topic_facet | Metallorganische Verbindungen Katalyse Einführung |
| url | http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=027624990&sequence=000003&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=027624990&sequence=000004&line_number=0002&func_code=DB_RECORDS&service_type=MEDIA |
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