Grignard reagents: new developments
Saved in:
| Format: | Book |
|---|---|
| Language: | English |
| Published: |
Chichester [u.a.]
Wiley
2000
|
| Subjects: | |
| Online Access: | Inhaltsverzeichnis |
| Physical Description: | XVI, 418 S. Ill., graph. Darst. |
| ISBN: | 0471999083 |
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| 300 | |a XVI, 418 S. |b Ill., graph. Darst. | ||
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Record in the Search Index
| _version_ | 1804127748698931200 |
|---|---|
| adam_text | Titel: Grignard reagents
Autor: Richey, Herman G
Jahr: 2000
Contents
List of Contributors xiii
Preface xv
1 Mechanistic Features of the Reactions of Organomagnesium Compounds 1
Torkil Holm and Ingolf Crossland
1.1 Introduction 1
1.2 Properties of Grignard Reagents 3
1.2.1 Thermochemistry 3
1.2.1.1 Heat of Formation of Grignard Reagents 3
1.2.1.2 C—Mg Bond Dissociation Energies 3
1.2.2 Oxidation Potentials of Grignard Reagents 4
1.2.3 Association Equilibria in Grignard Reagents 5
1.2.3.1 The Schlenk Equilibrium 5
1.2.3.2 Self Association in Grignard Reagents 5
1.2.3.3 Association between RMgX and Carbonyl Compounds 6
1.3 Reactions of Benzophenone(s) with Grignard Reagents 7
1.3.1 Prediction of a Radical Mechanism and Early Evidence 7
1.3.2 Reactivity Series and Linear Free Energy Correlations 8
1.3.3 Radical Probes 11
1.3.4 A Thermochemical Approach 13
1.3.5 Kinetic Isotope Effects 14
1.3.5.1 Isotopic Carbon and Hydrogen in Benzophenone 14
1.3.5.2 Deuterium Substitution in the Grignard Reagent 15
1.3.6 CIDNP Observations 16
1.3.7 A New School in the Study of the Reaction of Benzophenone with Grignard
Reagents 16
1.4 Polar Concerted Reaction Mechanisms 17
1.4.1 Addition to Aliphatic Ketones 17
1.4.2 Addition to Acid Derivatives 18
1.4.3 Concerted Transfer of ^-Hydrogen, Reduction 18
1.5 Reactions with ^^-Unsaturated Carbonyl Compounds 19
Contents
1.6 ET Substrates other than Benzophenone
1.6.1 Metal Catalysis
1.6.1.1 The Kharasch Reaction
1.6.1.2 Reductive Dimerization of Carbonyl Compounds
1.6.2 Reactions with Oxygen and with Peroxides
1.6.3 Reactions with Azobenzene
1.6.4 Reactions with Cinnamic Esters
1.7 Solvent Effects
1.8 Conclusion
2 Nucleophilic Displacements at Carbon by Grignard Reagents
E. Alexander Hill
2.1 Introduction
2.2 Survey of Coupling Reactions of Grignard Reagents with Organic Halides
2.2.1 Reactions with Simple AlkyI Halides
2.2.2 Reactions with Reactive Halides
2.3 Summary of Cross-coupling Mechanisms
2.3.1 Sn2 Displacement Mechanism
2.3.2 SnI Mechanism
2.3.3 Single Electron Transfer (SET) Mechanism
2.4 Mechanism of Grignard Cross-coupling Reactions
2.4.1 Saturated Alkyl Halides
2.4.1.1 Saturated and Aryl Grignard Reagents
2.4.1.2 Benzylic and Allylic Grignard Reagents
2.4.2 Benzylic and Allylic Halides
2.4.3 a-Haloethers and -Thioethers
2.5 Other Classes of Substrates
2.5.1 Arylmethyl Compounds
2.5.2 Polyhalogcn Compounds
2.5.3 a-Haloketones
2.5.4 Other Leaving Groups
2.5.4.1 Reaction with Carbocations—No Leaving Group
2.5.4.2 Oxy-Anions
2.5.4.3 Miscellaneous Leaving Groups
2.6 Some Related Topics
2.7 Summary and Conclusions
3 Hydromagncsiation of Alkenes and Alkynes
Eumie Sato and Hirokazu Urabe
3.1 Introduction
3.2 Hydromagnesiation of Alkenes
3.3 Hydromagnesiation of Conjugated Dienes
3.4 Hydromagnesiation of Alkynes
3.5 Application of Hydromagnesiation in Selective Synthesis of Natural Products
3.6 On the Mechanism of Cp2TiCl2-catalyzed Hydromagnesiation of Alkynes with
Grignard Reagents
3.7 Concluding Remarks
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Contents vii
4 Stereoselective Addition of Grignard Reagents to Alkenes 107
Amir H. Hoveyda, Nicola M. Heron and Jeffrey A. Adams
4.1 Introduction 107
4.2 Heteroatom-directed Addition of Grignard Reagents to Alkenes 108
4.3 Zr-Catalyzed Diastereoselective Carbomagnesation of Allylic and Homoallylic
Alcohols and Ethers 109
4.3.1 Zr-Catalyzed Diastereoselective Ethylmagnesation of Allylic Alcohols and Ethers 109
4.3.2 Zr-Catalyzed Diastereoselective Ethylmagnesation of Homoallylic
Alcohols and Ethers 112
4.4 Zirconocene-catalyzed Enantioselective Alkylation Reactions 114
4.4.1 Catalytic Enantioselective Alkylation of Alkenes with Alkylmagnesium Halides 114
4.4.2 Zr-Catalyzed Kinetic Resolution of Unsaturated Heterocycles 119
4.4.3 Zr-Catalyzed Kinetic Resolution of Cyclic Allylic Ethers 123
4.4.4 Related Catalytic Enantioselective Alkylation of Alkenes with Alkylaluminums 125
4.5 Ni-Catalyzed Stereoselective Alkylation of Alkenes with Grignard Reagents 126
4.5.1 Diastereoselective Ni-Catalyzed Addition of Grignard Reagents to Allylic Ethers 128
4.5.1.1 Directed Ni-catalyzed Addition of Grignard Reagents to Allylic Ethers 128
4.5.1.2 Ni-catalyzed Addition of Grignard Reagents to Bicyclic Allylic Ethers 131
4.5.2 Asymmetric Ni-Catalyzed Addition of Grignard Reagents to Allylic Ethers 132
4.5.3 Asymmetric Ni-Catalyzed Addition of Grignard Reagents to Allylic Acetals 134
4.6 Summary and Outlook 135
5 Stereoselective Additions of Chiral Grignard Reagents to Aldehydes: Stereochemical and
Mechanistic Principles, with Examples Using a-Amino Grignard Reagents 139
Robert E. Gawley
5.1 Introduction to Stereoselectivity in Grignard Additions 139
5.2 Transition States and Mechanistic Rationales 141
5.3 Topicity and Terminology 143
5.4 Additions of Configurationally Stable Grignards to Aldehydes 145
5.5 Configurational Lability of Benzylic Grignards 146
5.6 Additions of Benzylic Grignards to Aldehydes 148
5.7 Applications to Alkaloid Synthesis 153
5.8 Summary 162
6 Grignard Reagents—Industrial Applications and Strategy 165
Frank R. Busch and David M. De Antonis
6.1 Introduction 165
6.2 Safety and Engineering Considerations Specific to Industrial Applications 166
6.2.1 Typical Equipment Configuration 166
6.2.2 Choice of Solvent 167
6.2.3 Process Hazards Analysis 167
6.2.4 Vent Sizing/DIERS Calculations 168
6.2.5 Grignard Reagent Formation—Process Controls and Interlocks 168
6.2.5.1 Control of Exotherm 168
6.2.5.2 Safety Interlocks 170
VIII
Contents
6.2.6 Reactivity of Grignard Reagents—Water, Heating/Cooling Fluids 171
6.2.7 Safe Handling of Magnesium 17 J
6.3 Reaction Initiation *7^
6.3.1 Equipment Drying 172
6.3.2 Different Forms of Magnesium: Advantages and Disadvantages 172
6.3.3 Initiators—Advantages and Disadvantages 173
6.3.3.1 Vitride® 173
6.3.3.2 Small Portion of Grignard Reagent 174
6.3.3.3 Chemical Initiators 174
6.3.4 Detecting Initiation of Reaction 175
6.4 Examples of Industrial Grignard Chemistry 175
6.4.1 Tamoxifen 175
6.4.2 Droloxifcne 175
6.4.3 Veltol® and Veltol Plus® 176
6.4.4 Use of a Grignard Reagent as a Base (Formation of Magnesium Enolates) 176
6.4.5 Naproxen 178
6.4.6 Propoxyphene 180
6.4.7 Additional Examples 181
6.5 Waste Disposal 181
6.6 Summary 181
7 Mechanisms of Grignard Reagent Formation 185
John F. Garst and Ferenc Ungvary
7.1 Introduction 185
7.1.1 Grignard Reaction 185
7.1.2 Basic Facts 185
7.1.3 Overview 186
7.1.4 D and A Models 189
7.1.5 Occam s Razor 190
7.2 Organic Part of the Mechanism 191
7.2.1 Experimental Techniques 191
7.2.2 Rate Law
193
7.2.3 Radical Intermediates—Pathway R 193
7.2.4 Models, Rates, and Rate Constants 195
7.2.5 Kinetics of ZB and AB 198
7.2.6 Infinite-Dilution D Model 202
7.2.7 General D Model 203
7.2.8 Typical Alky! Halides 206
7.2.9 Cyclopropyl Halides 213
7.2.10 Vinyl Halides 222
7.2.11 Aryl Halides 222
7.2.12 Benzylic and Allylic Halides 225
7.2.13 Area of the Magnesium Surface 226
7.2.14 Concentration of Halide ^f.
7.2.15 Halogen
7.2.16 Solvent 229
7.2.17 Adamantyl Bromide 229
Contents
ix
7.2.18 Slurries of Small Magnesium Clusters 230
7.2.19 Chain Mechanisms 235
7.2.20 Carbanion Intermediates 235
7.2.21 Anion-Radical Intermediates in Reductions of Organic Halides 238
7.2.22 Retention of Configuration, Adsorption of R-, and the D Model 247
7.2.23 Arguments Against the D Model 248
7.2.24 Arguments Against the A Model 253
7.3 Inorganic Part of the Mechanism 253
7.3.1 Optical and Scanning-Electron Microscopy 253
7.3.2 Atomic-Force Microscopy (AFM) 254
7.3.3 Surface Spectroscopy 255
7.3.4 Initiation 255
7.3.5 Activation 257
7.3.6 Entrainment 259
7.3.7 Metallic Corrosion 259
7.3.8 Mg(I) Intermediates 260
7.3.9 Mgz-Solution Interface 262
7.3.10 Two Liquid Phases 263
7.3.11 Freckled Magnesium 264
7.4 Conclusions 266
Appendix 267
8 Applications of Magnesium Anthracene in Forming Grignard Reagents 277
Colin L. Raston
8.1 Introduction 277
8.2 Formation and Properties of Magnesium Anthracene 278
8.3 Reactions: General Considerations 281
8.4 Formation of Grignard Reagents 284
8.4.1 Mono-Grignard Reagents—Special Features 286
8.4.2 Di- and Tri-Grignard Reagents 288
8.4.3 Mechanism 289
8.5 Reactions of Other Organic Halides 290
8.6 Supported Magnesium Anthracene Complexes 293
8.6.1 Synthesis 293
8.6.2 Grignard Reagents 295
8.6.3 Polymer and Silica Recycling 296
8.7 Future Prospects 296
9 Structures of Organomagnesium Compounds as Revealed by X-ray Diffraction Studies 299
F. Bickelhaupt
9.1 Introduction 299
9.2 Magnesium with Coordination Number 2 300
9.3 Magnesium with Coordination Number 3 301
9.4 Simple Organomagnesium with Coordination Number 4 302
9.4.1 Mononuclear Compounds 302
9.4.2 Dimeric Compounds 304
9.4.3 Polymeric Compounds 305
Contents
9.5 Simple Organomagnesium with Coordination Number 5 and 6
9.5.1 Organomagnesium Compounds with Coordination Number 5
9.5.2 Organomagnesium Compounds with Coordination Number 6
9.6 Difunctional Organomagnesium Compounds
9.6.1 Simple Difunctional Organomagnesium Compounds
9.6.2 Organomagnesium Compounds Derived from Dienes or Diynes
9.6.3 Anthracenemagnesium Derivatives
9.7 Organomagnesium Compounds with Polyhapto Carbon Ligands
9.7.1 Cyclopentadienyl Derivatives and Related Compounds
9.7.2 Carborane Derivatives
9.8 Organomagnesium Compounds with Intramolecular and/or Polycoordination
9.8.1 Intramolecular Coordination
9.8.2 Intramolecular Polycoordination
9.8.3 Intermolecular Polycoordination
9.9 Heterometallic Organomagnesium Complexes
9.9.1 Heterometallic Organomagnesium Complexes with Alkali Metals
9.9.2 Heterometallic Organomagnesium Complexes with Aluminum
9.9.3 Heterometallic Organomagnesium Complexes with Transition Metals
9.10 Conclusions
10 X-ray Absorption Spectroscopy and Large Angle X-ray Scattering of Grignard Compounds
T.S. Ertel and H. Bertagnolli
10.1 Introduction
10.2 EXAFS
10.2.1 Theoretical Background
10.2.2 Measurement Fundamentals and Techniques
10.2.3 Data Analysis
10.3 LAXS
10.3.1 Theoretical Background
10.3.2 Measurement Fundamentals and Techniques
10.3.3 Data Analysis
10.4 Comparison of EXAFS and LAXS Techniques
10.5 Physical Chemistry of Grignard Compounds
10.5.1 Introduction
10.5.2 Crystallography
10.5.3 Molecular Weight Studies
10.5.4 Tracer Studies
10.5.5 Conductivity Measurements
10.5.6 Infrared Spectroscopy
10.5.7 NMR Spectroscopy
10.5.8 Theoretical Studies
10.6 EXAFS and LAXS of Grignard Compounds
10.6.1 Introduction
10.6.2 EXAFS Studies
10.6.3 LAXS Studies
10.7 Concluding Remark: Current Structural Picture
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Contents xi
11 Di- and Polyfunctional Organomagnesium Compounds 367
F. Bickelhaupt
11.1 Introduction 367
11.2 1,1-Di-organomagnesium Reagents 369
11.2.1 Synthesis and Structure 369
11.2.2 Applications 370
11.3 1,2-Di-organomagnesium Reagents 372
11.3.1 Synthesis and Structure 372
11.3.2 Applications 374
11.4 1,3-Di-organomagnesium Reagents 375
11.4.1 Synthesis and Structure 375
11.4.2 Applications 377
11.5 1,4- and Larger a, cu-Di-organomagnesium Reagents 380
11.5.1 Synthesis and Structure 380
11.5.2 Applications 382
11.6 Tri- and Polyorganomagnesium Reagents 385
11.7 Conclusion 389
12 Unusual Organomagnesium Compounds 395
V.V. Smirnov, LA. Tjurina and LP. Beletskaya
12.1 Introduction 395
12.2 Cluster Grignard Reagents 395
12.2.1 Metal Vapour Cryosynlhesis 395
12.2.2 The Role of Clusters in the Low-Temperature Cryosynthesis of Organomagnesium
Compounds 396
12.2.3 Cluster Grignard Reagents—Characterization 397
12.2.4 Cluster Grignard Reagents—Reactions with Organic Halides 399
12.3 Cluster Magnesium Hydrides 401
12.3.1 Theory 401
12.3.2 Magnesium-Hydrocarbon Cryosyntheses 403
12.3.2.1 Alkylbenzenes 403
12.3.2.2 Cyclopentadiene 404
12.3.2.3 Phenylacetylene 405
12.3.2.4 1-Alkenes 406
12.3.2.5 Anthracene 407
12.3.3 Catalytic Properties of Magnesium-Hydrocarbon Adducts 409
12.4 Conclusion 410
Index
411
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| indexdate | 2024-07-09T18:38:17Z |
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| spelling | Grignard reagents new developments ed. by Herman G. Richey Chichester [u.a.] Wiley 2000 XVI, 418 S. Ill., graph. Darst. txt rdacontent n rdamedia nc rdacarrier Chimie - Essais et réactifs ram Composés organomagnésiens Grignard, Réactifs de Grignard, Réactifs de ram Magnésium - Composés organiques ram Grignard reagents Grignard-Verbindungen (DE-588)4158201-9 gnd rswk-swf Grignard-Reaktion (DE-588)4158200-7 gnd rswk-swf Grignard-Reaktion (DE-588)4158200-7 s DE-604 Grignard-Verbindungen (DE-588)4158201-9 s Richey, Herman G. Sonstige oth HBZ Datenaustausch application/pdf http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=008892098&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA Inhaltsverzeichnis |
| spellingShingle | Grignard reagents new developments Chimie - Essais et réactifs ram Composés organomagnésiens Grignard, Réactifs de Grignard, Réactifs de ram Magnésium - Composés organiques ram Grignard reagents Grignard-Verbindungen (DE-588)4158201-9 gnd Grignard-Reaktion (DE-588)4158200-7 gnd |
| subject_GND | (DE-588)4158201-9 (DE-588)4158200-7 |
| title | Grignard reagents new developments |
| title_auth | Grignard reagents new developments |
| title_exact_search | Grignard reagents new developments |
| title_full | Grignard reagents new developments ed. by Herman G. Richey |
| title_fullStr | Grignard reagents new developments ed. by Herman G. Richey |
| title_full_unstemmed | Grignard reagents new developments ed. by Herman G. Richey |
| title_short | Grignard reagents |
| title_sort | grignard reagents new developments |
| title_sub | new developments |
| topic | Chimie - Essais et réactifs ram Composés organomagnésiens Grignard, Réactifs de Grignard, Réactifs de ram Magnésium - Composés organiques ram Grignard reagents Grignard-Verbindungen (DE-588)4158201-9 gnd Grignard-Reaktion (DE-588)4158200-7 gnd |
| topic_facet | Chimie - Essais et réactifs Composés organomagnésiens Grignard, Réactifs de Magnésium - Composés organiques Grignard reagents Grignard-Verbindungen Grignard-Reaktion |
| url | http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=008892098&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA |
| work_keys_str_mv | AT richeyhermang grignardreagentsnewdevelopments |