Modern arene chemistry: [concepts, synthesis, and applications]
Gespeichert in:
| Format: | Buch |
|---|---|
| Sprache: | English |
| Veröffentlicht: |
Weinheim
Wiley-VCH
2002
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| Schlagworte: | |
| Online-Zugang: | Inhaltsverzeichnis |
| Beschreibung: | XVIII, 617 S. zahlr. Ill., graph. Darst. |
| ISBN: | 3527304894 |
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| 245 | 1 | 0 | |a Modern arene chemistry |b [concepts, synthesis, and applications] |c ed. by Didier Astruc |
| 264 | 1 | |a Weinheim |b Wiley-VCH |c 2002 | |
| 300 | |a XVIII, 617 S. |b zahlr. Ill., graph. Darst. | ||
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Datensatz im Suchindex
| _version_ | 1804129440855228416 |
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Contents
List of Contributors xvi
Arene Chemistry: From Historical Notes to the State of the Art 1
Didier Astruc
The History of Benzene 1
The History of Aromaticity 5
Some Key Trends Towards Modern Arene Chemistry 9
Aromatic Chemistry: From the 19th Century Industry to the State of the
Art 11
Organization of the Book and Content 13
References 16
1 The Synthesis of Tris-Annulated Benzenes by Aldol Trimerization of Cyclic
Ketones 20
Margaret M. Boorum and Lawrence T. Scott
Abstract 20
1.1 Introduction 20
1.2 Truxene and Truxone: Venerable Prototypes 21
1.3 Other Examples 23
1.4 Lirmtations 27
1.4.1 Experimental Observations and a Working Hypothesis 27
1.4.2 Guidance from Calculations 29
1.5 Conclusions 30
References 31
2 Oligounsaturated Five-Membered Carbocycles — Aromatic and Antiaromatic
Compounds in the Same Family 32
Rainer Haag and Armin de Meijere
Abstract 32
2.1 Introduction 32
2.2 Cyclopentadienyl Cations 33
2.3 Fulvene and Spiroannelated Cyclopentadiene Derivatives 37
vi I Contents
2.4 Polyunsaturated Di-, Tn-, and Oligoquinanes 38
2.4.1 Pentalene, Pentalenediide, and Pentalene Metal Complexes 39
2.4.2 Acepentalene, Acepentalenediide, and Acepentalene Metal Complexes 42
2.4.3 Generation of C2o-Fullerene 44
References 50
3 The Suzuki Reaction with Arylboron Compounds in Arene Chemistry 53
Äkira Suzuki
Abstract 53
3.1 Intioduction 53
3.2 Reactions with Aryl Halides and Triflates: Synthesis of Biaryls 54
3.2.1 Aromatic-Aromatic Couplmg 54
3.2.2 Aromatic-Heteroaromatic and Heteroaromatic-Heteroaromatic Couplings 65
3.2.3 Coupling of Arylboron Compounds Bearing Sterically Bulky or Electron-
Withdrawing Substituents 76
3.2.4 Modified Catalysts and Ligands 80
3.2.5 Solid-Phase Synthesis (Combinatonal Mefhodology) 84
3.3 Reactions with 1-Alkenyl Halides and Triflates 88
3.4 Reactions with Aryl Chlorides and Other Organic Electrophiles 93
3.5 Miscellaneous 98
3.6 Applications in Polymer Chemistry 99
References 102
4 Palladium-Catalyzed Amination of Aryl Halides and Sulfonates 107
John F. Hartwig
Abstract 107
4.1 Introduction 107
4.1.1 Synthetic Considerations 107
4.1.2 Prior C-X Bond-Forming Coupling Chemistry Related to the Amination of Aryl
Halides 108
4.1.3 Novel Organometallic Chemistry 109
4.1.4 Organization of the Review 109
4.2 Background 110
4.2.1 Early Palladium-Catalyzed Amination 110
4.2.2 Initial Synthetic Problems to be Solved 111
4.3 Palladium-Catalyzed Amination of Aryl Halides with Amine
Substrates 111
4.3.1 Early Work 111
4.3.1.1 Initial Intermolecular Tin-Free Aminations of Aryl Halides 111
4.3.1.2 Initial Intramolecular Amination of Aryl Halides 112
4.3.2 Second Generation Catalysts: Aryl Bis-phosphines 212
4.3.2.1 Amination of Aryl Halides 112
4.3.2.2 Amination of Aryl Triflates 115
4.3.2.3 Amination of Heteroaromatic Halides 116
4.3.2.4 Aminations of Solid-Supported Aryl Halides 119
Contents vii
4.3.2.5 Amination of Polyhalogenated Aromatic Substrates 119
4.3.3 Third-Generation Catalysts with Alkylmonophosphines 119
4.3.3.1 High-Temperature Aminations Involving P(tBu)3 as Ligand 120
4.3.3.2 Use of Sterically Hindered Bis(phosphine) Ligands 220
4.3.3.3 P,N Ligands and Dialkylphosphinobiaryl Ligands 121
4.3.3.4 Phenyl Backbone-Derived P,0 Ligands 123
4.3.3.5 Low-Temperature Reactions Employing P(tBu)3 as a Ligand 124
4.3.3.6 Heterocyclic Carbenes as Ligands 124
4.3.37 Phosphine Oxide Ligands 128
4.3.4 Heterogeneous Catalysts 129
4.4 Aromatic C-N Bond Formation with Non-Amine Substrates and Ammonia
Surrogates 129
4.4.1 Amides, Sulfonamides, and Carbamates 130
4.4.2 Allylamine as an Ammonia Surrogate 131
4.4.3 Imines 132
4.4.4 Protected Hydrazines 132
4.4.5 Azoles 133
4.5 Amination of Base-Sensitive Aryl Halides 235
4.6 Applications of the Amination Chermstry 236
4.6.1 Synthesis of Biologically Active Molecules 236
4.6.1.1 Arylation of Secondary Alkylamines 136
4.6.1.2 Arylation of Primary Alkylamines 238
4.6.2 Applications in Materials Science 242
4.6.2.1 Polymer Synthesis 242
4.6.2.2 Synthesis of Discrete Oligomers 243
4.6.2.3 Synthesis of Azacyclophanes 246
4.6.2.4 Synthesis of Small Molecules for Materials Applications 246
4.6.3 Palladium-Catalyzed Amination in Ligand Synthesis 247
4.7 Mechanism of Aryl Halide Amination and Etheration 249
4.7.1 Oxidative Addition of Aryl Halides to L2Pd Complexes (L = P(o-tolyl)3, BINAP,
DPPF) and lts Mechanism 249
4.7.2 Formation of Amido Intermediates 252
4.7.2.1 Mechanism of Palladium Amide Formation from Amines 252
4.7.3 Reductive Eliminations of Amines from Pd(II) Amido Complexes 252
4.7.4 Competing /i-Hydrogen Elimination from Amido Complexes 255
4.7.5 Selectivity: Reductive Elimination vs. //-Hydrogen Elimination 256
4.7.6 Overall Catalytic Cycle with Specific Intermediates 258
4.7.6.1 Mechanism for Amination Catalyzed by P(o-C6H4Me)3 Palladium
Complexes 258
4.7.6.2 Mechanism for Amination Catalyzed by Palladium Complexes with Chelating
Ligands 259
4.7.6.3 Mechanism of Amination Catalyzed by Palladium Complexes with Sterically
Hindered Alkyl Monophosphines 260
4.8 Summary 260
References 262
viii I Contents
5 From Acetylenes to Aromatics: Novel Routes - Novel Products 169
Henning Hopf
Abstract 169
5.1 Introduction 269
5.2 The Aromatization of Hexa-l,3-dien-5-yne to Benzene: Mechanism and
Preparative Applications 171
5.3 The Construction of Extended Aromatic Systems from Ethynyl Benzene
Derivatives 177
5.4 Bridged Aromatic Hydrocarbons Containing Triple Bonds (Cyclophynes) 187
References 192
6 Functional Conjugated Materials for Optonics and Electronics by Tetraethynylethene
Molecular Scaffolding 296
Mogens Br0ndsted Nielsen and Frangois Die.de.rich
Abstract 196
6.1 Introduction 296
6.2 Arylated Tetraethynylethenes 298
6.2.1 Nonlinear Optical Properties 198
6.2.2 Photochemically Controlled ds-trans Isomerization: Molecular Switches 299
6.2.3 Electrochemically Controlled ds-trans Isomerization 202
6.3 Tetraethynylethene Dimers 202
6.4 Two-Dimensional Scaffolding: Expanded Carbon Cores 204
6.4.1 Perethynylated Dehydroannulenes 204
6.4.2 Perethynylated Expanded Radialenes 205
6.4.3 Cyclic Platinum a-Acetylide Complex of Tetraethynylethene 208
6.5 Linearly ^-Conjugated Oligomers and Polymers: Poly(triacetylene)s 209
6.5.1 Lateral Aryl Substitution 210
6.5.2 Aromatic Spacer Units 220
6.5.3 Donor-Donor and Acceptor-Acceptor End-Functionalization 212
6.6 Conclusions 212
Abbreviations 223
References 223
7 The ADIMET Reaction: Synthesis and Properties of
Poly(dialkylporophenyleneethynylene)s 217
Uwe H. F. Bum
Abstract 227
7.1 Introduction 227
7.1.1 Scope and Coverage of this Review 227
7.1.2 Historical Perspective 217
7.2 Syntheses 220
7.2.1 PPEs by Acyclic Diyne Metathesis (ADIMET) Utilizing Schrock s Tungsten
Carbyne Complex 220
7.2.2 Synthesis of Diarylalkynes Utilizing the Mori System 222
Contents ix
7.2.3 Cycles 223
7.2.4 Alkyne-Bridged Polymers by ADIMET 225
7.3 Reactivities of PPEs 229
7.4 Solid-State Structures and Liquid-Crystalline Properties of the PPEs 231
7.4.1 Organometallic Poly(aryleneethynylene)s 231
1 A.I Poly(dialkylparaphenyleneefhynylene)s 233
7.5 Spectroscopic Properties of Dialkyl-PPEs 235
7.5.1 UV/vis Spectroscopy of Dialkyl-PPEs 237
7.5.2 Fluorescence Spectroscopy: The Excited State Story 240
7.6 Self-Assembly of PPEs on Surfaces: From Jammed Gel Phases to Nanocables
and Nanowires 242
7.7 PPE-Based Organic Light-Emitting Diodes (OLEDs) 244
7.8 Conclusions and Outlook 245
References 247
8 The Chromium-Templated Carbene Benzannulation Approach to Densely
Functionalized Arenes (Dotz Reaction) 250
Karl Heinz Dotz and Joachim Stendeljr.
Abstract 250
8.1 Introduction 250
8.2 Mechanism and Chemoselectivity of the Benzannulation 253
8.2.1 Mechanism 253
8.2.2 Chemoselectivity 255
8.3 Scope and Limitations 257
8.3.1 The Carbene Complex 257
8.3.1.1 Availability 257
8.3.1.2 The Carbene Ligand 259
8.3.1.3 The Chromium Template 263
8.3.2 The Alkyne 264
8.3.3 Regioselectivity 265
8.3.4 Diastereoselectivity 269
8.3.5 Thermal and Photochemical Benzannulation 271
8.3.6 Subsequent Transformations 271
8.4 Typical Experimental Procedure 272
8.5 Synthesis of Specific Arenes 273
8.5.1 Biaryls 273
8.5.2 Cyclophanes 275
8.5.3 Annulenes and Dendritic Molecules 278
8.5.4 Angular, Linear, and Other Fused Polycyclic Arenes 279
8.5.5 Fused Heterocycles 283
8.6 Synthesis of Biologically Active Compounds 285
8.6.1 Vitamins 285
8.6.2 Antibiotics 286
8.6.3 Steroids 289
x Contents
8.6.4 Alkaloids 290
8.7 Summary and Outlook 291
References 292
9 Osmium- and Rhenium-Mediated Dearomatization Reactions with Arenes 297
Mark X Valahovic, Joseph M. Keane, and W. Dean Harman
Abstract 297
9.1 Introduction 297
9.2 {Os(NH3)5}2+ - The Pentaammmeosmium(II) Fragment 298
9.2.1 Preparation of r]2-Arene Complexes 298
9.2.2 Binding Selectivity 298
9.2.3 Hydrogenations 299
9.2.4 Benzene and Alkylated Benzenes 300
9.2.4.1 Benzene 300
9.2.4.2 Toluene 301
9.2.4.3 Xylenes 302
9.2.5 Naphthalene 302
9.2.5.1 Tandem Addition Reactions 303
9.2.5.2 Cydizations 304
9.2.6 Anisole 306
9.2.6.1 Electrophilic Substitutions 306
9.2.6.2 Tandem Additions 306
9.2.6.3 Cyclization Reactions 310
9.2.7 Aniline 315
9.2.7.1 Electrophilic substitution 315
9.2.7.2 4H-Anilinium Michael Additions 316
9.2.7.3 Electrophilic Addition Reactions 318
9.2.7.4 Michael-Michael-Michael Ring-Closure 318
9.2.8 Phenol 318
9.2.8.1 Electrophilic Substitution Reactions 318
9.2.8.2 Michael Addition Reactions 320
9.2.8.3 o-Quinone Methide Complexes 323
9.3 {TpRe(CO)(L)} 323
9.3.1 Introduction 323
9.3.2 Preparation of 72-Arene Complexes 324
9.3.3 Quadrant Analysis 324
9.3.4 Naphthalene 324
9.3.5 Cycloadditions 326
9.4 Concluding Remarks 328
References 328
10 The Directed ortho Metalation Reaction - A Point of Departure for New Synthetic
Aromatic Chemistry 330
Christian G. Hartung and Victor Snieckus
Abstract 330
Contents xi
10.1 Introduction 330
Aims of this Account 330
10.2 The DoM Reaction as a Methodological Tool 332
10.2.1 The N-Cumyl Carboxamide, Sulfonamide, and O-Carbamate DMGs 333
10.2.2 The Lithio Carboxylate and Carboxylate Ester DMGs 334
10.2.3 The Di-tert-Butyl Phosphme Oxide DMG 336
10.3 Heteroaromatic Directed oriho Metalation (HetDoM) in Methodological
Practice 337
10.3.1 n-Excessive Heteroaromatic Directed oriho Metalation (HetDoM) 337
10.3.1.1 Furans and Thiophenes 337
10.3.1.2 Indoles 339
10.3.2 7t-Deficient Heteroaromatic Directed oriho Metalation (HetDoM) 342
10.3.2.1 Pyndines 342
10.4 The DoM-Transition Metal Catalyzed Aryl-Aryl Cross-Coupling
Symbiosis 344
10.4.1 The Suzuki-Miyaura-DoM Link 345
10.4.2 Aryl O-Carbamate and S-Thiocarbamate-Grignard Cross-Coupling
Reactions 346
10.4.3 The DoM-Negishi Cross-Coupling Connection 349
10.4.4 DoM-Derived Cross-Coupling Reactions. Synthetic Comparison of Boron, Zinc,
and Magnesium Coupling Partners 350
10.5 Beyond DoM: The Directed Remote Metalation (DreM) of Biaryl Amides and
O-Carbamates - New Methodologies for Condensed Aromatics and
Heteroaromatics 351
10.5.1 Heteroatom-Bridged Biaryl DreM. General Anionic Friedel-Crafts
Complements for Several Classes of Heterocycles 356
10.6 Interfacing DoM with Emerging Synthetic Methods 359
10.7 Closing Comments 362
References 363
11 Arenetricarbonylchromium Complexes: Ipso, Cine, Tele Nucleophilic Aromatic
Substitutions 368
Frangoise Rose-Munch and Eric Rose
Abstract 368
11.1 Introduction 368
11.1.1 Effects on Arene Reactivity of Cr(CO)3 Coordination 368
11.1.2 Coverage and Definitions 369
11.2 Ipso Nucleophilic Aromatic Substitutions 372
11.2.1 Carbon-Oxygen, -Sulfur and -Selenium Bond Formation 372
11.2.2 Carbon-Nitrogen and Carbon-Phosphorus Bond Formation 378
11.2.3 Carbon-Carbon Bond Formation 383
11.2.4 Carbon-Hydrogen and Carbon-Metal Bond Formation 389
11.3 Cine and Tele Nucleophilic Aromatic Substitutions 392
11.3.1 Cleavage of C-F and C-Cl Bonds 392
11.3.2 Cleavage of C-0 Bonds 394
xii Contents
11.3.3 Cleavage of C-N Bonds 395
11.4 Concluding Remarks 396
Abbreviations 396
References 397
12 Activation of Simple Arenes by the CpFe+ Croup and Applications to the Synthesis of
Dendritic Molecular Batteries 400
Didier Astruc, Sylvain Nlate, and Jaime Ruiz
Abstract 400
12.1 Introduction 400
12.2 General Features of the CpFe+Activation of Arenes 401
12.2.1 Complexation and Decomplexation 401
12.2.2 Solubility, Stability, and General Reactivity Trends 402
12.2.3 Single-Electron Reduction and Oxidation 403
12.2.4 Deprotonation 403
12.2.5 Reaction of the 19-Electron Fe1 Complex with O2: Extraordinary Reactivity of
Naked Superoxide and its Inhibition 404
12.2.6 Nudeophilic Reactions 405
12.2.7 Heterolytic Cleavage of Aryl Ethers 406
12.3 CpFe+-Induced Hexafunctionalization of Hexamethylbenzene for the Synthesis
of Metallo-Stars 406
12.4 CpFe+-Induced Octafunctionalization of Durene in the Synthesis of
Metallodendnmer Precursors 411
12.5 CpFe+-Induced Triallylation of Toluene and Reactivity of the Triallyl Tripod
Towards Transition Metals 413
12.6 Nonaallylation of Mesitylene for the Synthesis of Dendritic Precursors of Large
Metallodendrimers 414
12.7 CpFeMnduced Activation of Ethoxytoluene in the One-Pot Synthesis of a
Phenol Dendron by Triple-Branching and Synthesis of Organometallic
Dendrons 419
12.8 Convergent and Divergent Syntheses of Large Ferrocenyl Dendrimers with
Good Redox Stabilities 421
12.9 Polyferrocenium Dendrimers: Molecular Batteries? 426
12.10 Large Dendrimers Functionalized on their Branches by the Electron-Reservoir
[FeCp( 76-C6Me6)]+ Groups: A Molecular Battery in Action 428
12.11 Conclusion 429
References 431
13 Charge-Transfer Effects on Arene Structure and Reactivity 435
Sergiy V. Rosokha and Jay K. Kochi
Abstract 435
13.1 I ntroduction 435
13.2 Mullikerfs Quantitative Description of Intermolecular (Charge-Transfer)
Complexes 436
Contents I xiii
13.2.1 Short Theoretical Background 436
13.2.2 Quantitative Evaluation of Arenes as Electron Donors 437
13.2.3 Spectral (UV/vis) Probe for the Formation of CT Complexes 438
13.2.4 IR Spectroscopic Studies of Charge-Transfer Complexation 442
13.2.5 Thermodynamics of Charge-Transfer Complexation 443
13.3 Structural Features of Arene Charge-Transfer Complexes 445
13.3.1 Bonding Distance of the Donor/Acceptor Dyad in Arene Complexes 446
13.3.2 Relationship Between Hapticity and Charge Transfer in Arene Complexes 447
13.3.3 Effect of Charge Transfer on the Structural Features of Coordinated
Arenes 448
13.3.3.1 Expansion of the Arene Ring 448
13.3.3.2 7i-Bond Localization in the Arene Ring 449
13.3.3.3 Loss of Plananty of the Arene Ring and the Transition from n- to a-
Binding 451
13.4 Charge-Transfer Activation of Coordinated Arenes 452
13.4.1 Carbon-Hydrogen Bond Activation 453
13.4.2 Nucleophilic/Electrophilic Umpolung 455
13.4.3 Modification of the Donor/Acceptor Properties of Coordinated Arene
Ligands 457
13.5 CT Complexes as Critical Intermediates in Donor/Acceptor Reactions of
Arenes 460
13.5.1 Effects of the Donor/Acceptor Interaction on the ET Dynamics of Arene
Donors 461
13.5.1.1 Steric Control of the Inner/Outer-Sphere Electron Transfer 461
13.5.1.2 Thermal and Photochemical ET in Strongly Coupled CT Complexes 463
13.5.2 Electron-Transfer Paradigm for Arene Transformation via CT Complexes 465
13.5.3 Electron-Transfer Activation of Electrophilic Aromatic Substitution 469
13.5.4 Structural Pre-organization of the Reactants in CT Complexes 470
13.5.5 CT Complexes in Aromatic Nitration and Nitrosation 472
13.6 Concluding Summary 475
References 475
14 Oxidative Aryl-Coupling Reactions in Synthesis 479
Guillaume, Lessme and Ken S. Fddman
Abstract 479
14.1 Introduction 479
14.2 Mechanistic Overview 480
14.3 Oxidative Coupling Reactions with Hypervalent Iodine Reagents 484
14.4 Other Reagents for the Oxidative Coupling Reaction 495
14.4.1 Iron(III) 495
14.4.2 Vanadium, Thallium, and Lead 499
14.4.3 Copper(II) 504
14.4.4 Electrochemical Methods 509
14.4.5 Other Metals 510
xiv I Contents
14.4.6 Non-Metal Mediated Methods 513
14.5 Phase-Supported Oxidants 525
14.5.1 Reagents Supported on Inorganic Materials 515
14.5.2 Polymer-Supported Hypervalent Iodine Reagents 515
14.6 Control of Atropisomerism 517
14.6.1 Transfer of Chiral Information via the Molecular Backbone 518
14.6.2 Oxidative Coupling of Two Chiral Molecules 524
14.6.3 Stoichiometric Chiral Oxidation Reagents 524
14.6.4 Catalytic Enantioselective Oxidative Coupling 527
14.7 Conclusion 534
References 535
15 Oxidative Conversion of Arenols into ortho-Quinols and ortho-Quinone Monoketals -
A Useful Tactic in Organic Synthesis 539
Stephane Quideau
Abstract 539
15.1 Introduction 539
15.1.1 How to Prepare ortho-Quinols and ortho-Quinone Monoketals 540
15.1.2 Why Bother with ortho-Qumols and ortho-Quinone Monoketals? 542
15.1.2.1 Synthetic Reactivity of ortho-Qumols and ortho-Quinone Monoketals 542
15.1.2.2 Biosynfhetic Implications of ortho-Quinols and ortko-Quinone Monoketals 543
15.1.2.3 Biomechanistic Implications of ortho-Quinols and ortko-Quinone
Monoketals 545
15.2 Oxidative Dearomatization of orthoSubstituted Arenols 546
15.2.1 Anodic Oxidation 546
15.2.2 Metal-Based Oxidative Activation 548
15.2.3 Halogen-Based Reagents 550
15.3 Synthetic Applications of ortho-Quinols and ortfio-Qumone Monoketals 554
15.3.1 Diels-Alder Cycloadditions 554
15.3.2 Photochemical Rearrangements 561
15.3.3 Nucleophilic Substitutions and Additions 563
15.4 Conclusion 568
References 568
16 Molecular Switches and Machines Using Arene Building Blocks 574
Hsian-Rong Tseng and J. Fraser Stoddart
Abstract 574
16.1 Introduction 574
16.2 From Self-Assembling [2]Catenanes to Electronic Devices 575
16.3 A Hybrid (2]Catenane Switch 580
16.4 A Self-Complexing Molecular Switch 581
16.5 Pseudorotaxane-Based Supramolecular Machines 582
16.6 [2]Rotaxanes and Molecular Shuttles 583
16.7 The Evolution of Photochemically Driven Molecular Switches 589
16.8 Chemically Switchable Pseudorotaxanes 594
Contents I xv
16.9 Molecule-Based XOR Logic Gate 596
16.10 Conclusions 597
References 597
Index 600
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| discipline | Chemie / Pharmazie Chemie |
| format | Book |
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| id | DE-604.BV014693494 |
| illustrated | Illustrated |
| indexdate | 2024-07-09T19:05:11Z |
| institution | BVB |
| isbn | 3527304894 |
| language | English |
| oai_aleph_id | oai:aleph.bib-bvb.de:BVB01-009965762 |
| oclc_num | 248804008 |
| open_access_boolean | |
| owner | DE-355 DE-BY-UBR DE-29T DE-19 DE-BY-UBM DE-91G DE-BY-TUM DE-20 DE-703 DE-1102 DE-11 |
| owner_facet | DE-355 DE-BY-UBR DE-29T DE-19 DE-BY-UBM DE-91G DE-BY-TUM DE-20 DE-703 DE-1102 DE-11 |
| physical | XVIII, 617 S. zahlr. Ill., graph. Darst. |
| publishDate | 2002 |
| publishDateSearch | 2002 |
| publishDateSort | 2002 |
| publisher | Wiley-VCH |
| record_format | marc |
| spelling | Modern arene chemistry [concepts, synthesis, and applications] ed. by Didier Astruc Weinheim Wiley-VCH 2002 XVIII, 617 S. zahlr. Ill., graph. Darst. txt rdacontent n rdamedia nc rdacarrier Aromaten Aromaten (DE-588)4143049-9 gnd rswk-swf Aromaten (DE-588)4143049-9 s DE-604 Astruc, Didier Sonstige (DE-588)112945058 oth HBZ Datenaustausch application/pdf http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=009965762&sequence=000002&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA Inhaltsverzeichnis |
| spellingShingle | Modern arene chemistry [concepts, synthesis, and applications] Aromaten Aromaten (DE-588)4143049-9 gnd |
| subject_GND | (DE-588)4143049-9 |
| title | Modern arene chemistry [concepts, synthesis, and applications] |
| title_auth | Modern arene chemistry [concepts, synthesis, and applications] |
| title_exact_search | Modern arene chemistry [concepts, synthesis, and applications] |
| title_full | Modern arene chemistry [concepts, synthesis, and applications] ed. by Didier Astruc |
| title_fullStr | Modern arene chemistry [concepts, synthesis, and applications] ed. by Didier Astruc |
| title_full_unstemmed | Modern arene chemistry [concepts, synthesis, and applications] ed. by Didier Astruc |
| title_short | Modern arene chemistry |
| title_sort | modern arene chemistry concepts synthesis and applications |
| title_sub | [concepts, synthesis, and applications] |
| topic | Aromaten Aromaten (DE-588)4143049-9 gnd |
| topic_facet | Aromaten |
| url | http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=009965762&sequence=000002&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA |
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