Lithium compounds in organic synthesis: from fundamentals to applications
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| Sprache: | English |
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2014
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| Beschreibung: | XXIV, 545 S. Ill., graph. Darst. 244 mm x 170 mm |
| ISBN: | 3527333436 9783527333431 9783527667512 |
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Datensatz im Suchindex
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VII
CONTENTS
LIST OF CONTRIBUTORS XV
FOREWORD
XXI
PREFACE XXIII
PARTI NEW STRUCTURAL ASPECTS OF LITHIUM COMPOUNDS 1
1 STRUCTURE-REACTIVITY RELATIONSHIP IN ORGANOLITHIUM COMPOUNDS 3
ELENA CARL AND DIETMAR STALKE
1.1 STRUCTURAL PRINCIPLES IN ORGANOLITHIUM COMPOUNDS 3
1.2 DONOR-BASE-FREE STRUCTURES 4
1.2.1 TETRAMERS 4
1.2.2 HEXAMERS 6
1.2.3 COMPARISON OF [ME
3
SICH
2
LI]
6
AND [N-BULI]
6
7
1.3 DISAGGREGATION WITH LEWIS BASES 8
1.3.1 TETRAMERS OF ALKYLLITHIUM COMPOUNDS 9
1.3.2 ASYMMETRIC AGGREGATES OF [ME
3
SICH
2
LI] (4) 11
1.3.3 AN OCTAMERIC AGGREGATE OF [ME
3
SICH
2
LI]
6
12
1.4 DONOR-BASE-INDUCED DIMERS AND MONOMERS 17
1.4.1 ALKYLLITHIUM AND TRIMETHYLSILYLMETHYLLITHIUM COMPOUNDS 17
1.4.2 PMDETA AGGREGATED MONOMERS 24
1.5 HETEROBIMETALLIC ORGANOLITHIUM COMPOUNDS 25
1.6 CONCLUSION AND OUTLOOK 28
REFERENCES 29
FURTHER READING 31
2 COMPUTATIONAL PERSPECTIVES ON ORGANOLITHIUMS 33
STEN O. NILSSON LILL
2.1 INTRODUCTION 33
2.2 THE NATURE OF BONDS TO LITHIUM 34
2.3 AGGREGATION OF LITHIUM ORGANIC COMPOUNDS 35
2.4 SOLVATION EFFECTS 36
2.5 LITHIUM ALKOXIDES AND LITHIUM AMIDES 41
2.6 COMPUTATIONAL STUDIES ON VARIOUS ORGANOLITHIUM APPLICATIONS 43
HTTP://D-NB.INFO/1042297428
VIIII
CONTENTS
2.7 CONCLUSION AND OUTLOOK 46
REFERENCES 47
FURTHER READING 51
3 SPECTROSCOPIC ADVANCES IN ORGANOLITHIUM REACTIVITY: THE CONTRIBUTION
OF RAPID-INJECTION NMR (RINMR) 53
AMANDA C. JONES
3.1 INTRODUCTION 53
3.2 THE CURTIN-HAMMETT PRINCIPLE 54
3.3 ORGANOLITHIUM NMR 55
3.4 FEATURES OF RINMR 58
3.4.1 BRIEF HISTORY 58
3.4.2 APPARATUS DESCRIPTIONS AND RAPIDITY OF ACQUISITION 59
3.4.3 TEMPERATURE RANGE AND CONTROL 60
3.4.4 VOLUME ACCURACY OF INJECTION 61
3.5 USE OF RINMR TO STUDY ORGANOMETALLIC REACTIONS 61
3.5.1 N-BUTYLLITHIUM AGGREGATE REACTIVITY (1985) 61
3.5.2 MAGNESIUM CHELATES IN CARBONYL ADDITIONS (1987/1990) 64
3.5.3 LITHIUM ENOLATE ALDOL (1992) 65
3.5.4 ALKYLLITHIUM POLYMERIZATION (1995/1999) 66
3.5.5 TIN TRANSMETALLATION (2007) 67
3.5.6 CUPRATES (2002-PRESENT)
68
3.5.7 N-BULI AGGREGATE REACTIVITY REVISITED (2007) 72
3.5.8 TRIS(TRIMETHYLSILYL)METHYLLITHIUM (2008/2009) 74
3.5.9 ENOLIZATION AND LITHIUM ALDOL (2011) 78
3.6 CONCLUSION AND OUTLOOK 80
REFERENCES 80
FURTHER READING 84
4 SPECTROSCOPIC ADVANCES IN STRUCTURAL LITHIUM CHEMISTRY:
DIFFUSION-ORDERED SPECTROSCOPY AND SOLID-STATE NMR 85
MURIEL SEBBAN, LAURE GUILHAUDIS, AND HASSAN OULYADI
4.1 GENERAL INTRODUCTION 85
4.2 APPLICATION OF SOLUTION NMR TO THE STRUCTURAL CHARACTERIZATION OF
ORGANOLITHIUM COMPOUNDS 86
4.2.1 DIFFUSION NMR MEASUREMENT METHODS 88
4.2.1.1 PULSED FIELD GRADIENT SPIN ECHO (PFGSE) 88
4.2.1.2 FROM THE FIRST TO THE SECOND DIMENSION: DOSY NMR
EXPERIMENT 89
4.2.2 DOSY APPLICATION TO THE STRUCTURAL ANALYSIS OF ORGANOLITHIUM
COMPOUNDS 90
4.2.2.1 STRUCTURE OF THE MIXED METHYLLITHIUM/LITHIUM CHLORIDE
AGGREGATE 97
4.2.2.2 STRUCTURE OF A LITHIUM PHOSPHIDO-BORANE 99
4.2.2.3 STRUCTURE OF LITHIUM ZINCATE 101
CONTENTS IX
4.2.3 CONCLUSION 104
4.3 SOLID-STATE NMR 104
4.3.1 BASIC PRINCIPLES 105
4.3.1.1 HOMO AND HETERONUCLEAR DIPOLE-DIPOLE COUPLINGS
(D: DIPOLE-DIPOLE) 105
4.3.1.2 CHEMICAL SHIFT ANISOTROPY (CSA) 105
4.3.1.3 QUADRUPOLAR INTERACTIONS FOR NUCLEI WITH I 1/2(Q) 105
4.3.1.4 MAGIC ANGLE SPINNING (MAS) 106
4.3.1.5 HIGH-POWER HETERONUCLEAR DECOUPLING 107
4.3.1.6 CROSS POLARIZATION - HARTMANN-HAHN CONDITION 107
4.3.2 SOLID-STATE NMR - APPLICATIONS TO ORGANOLITHIUM COMPOUNDS 108
4.3.2.1 STRUCTURE OF LITHIUM ALKYL AND ARYL COMPLEXES STABILIZED BY
NITROGEN
LIGANDS 108
4.3.2.2 SYMMETRY AND GEOMETRY OF FORMED STRUCTURES: C1P, SSIP,
SANDWICH 109
4.3.2.3 MOLECULAR DYNAMICS 113
4.3.2.4 REACTION MONITORING 113
4.3.3 CONCLUSION AND OUTLOOK 117
REFERENCES 117
FURTHER READING 121
5 MIXED LITHIUM COMPLEXES: STRUCTURE AND APPLICATION IN SYNTHESIS 123
ROBERT
E. MULVEY AND CHARLES T. O'HARA
5.1 INTRODUCTION 123
5.2 STRUCTURAL CHEMISTRY OF HETEROMETALLIC LITHIUM COMPLEXES 123
5.2.1 MIXED LITHIUM-SODIUM COMPLEXES 124
5.2.2 MIXED LITHIUM-POTASSIUM COMPLEXES 127
5.2.3 MIXED LITHIUM-MAGNESIUM COMPLEXES 129
5.2.4 MIXED LITHIUM-ZINC COMPLEXES 135
5.3 STRUCTURAL CHEMISTRY OF HETEROANIONIC LITHIUM COMPLEXES 139
5.4 SYNTHETIC APPLICATIONS OF LITHIUM MAGNESIATES: TURBO-GRIGNARD
REAGENTS 142
5.5 CONCLUSION AND OUTLOOK 146
REFERENCES 146
FURTHER READING 150
PART II NEW SYNTHETIC METHODOLOGIES BASED ON LITHIUM
COMPOUNDS 151
6 OXYGEN-BEARING LITHIUM COMPOUNDS IN MODERN SYNTHESIS 153
FILIPPO M. PERNA, ANTONIO SALOMONE, AND VITO CAPRIATI
6.1 INTRODUCTION 153
6.2 A-LITHIATED OXYGEN-SUBSTITUTED COMPOUNDS 153
6.2.1 ACYCLIC A-ALKOXY ORGANOLITHIUMS 155
6.2.1.1 NONSTABILIZED A-ALKOXY ORGANOLITHIUMS 155
XI CONTENTS
6.2.1.2 DIPOLE-STABILIZED A-ALKOXY ORGANOLITHIUMS 158
6.2.2 CYCLIC A-ALKOXY ORGANOLITHIUMS 163
6.2.2.1 A-LITHIATED OXIRANES 163
6.2.2.2 A-LITHIATED OXETANES 171
6.2.2.3 MISCELLANEOUS 173
6.3 ORTHO-LITHIATED OXYGEN-BEARING AROMATIC COMPOUNDS 177
6.4 REMOTE LITHIATED OXYGEN-BEARING COMPOUNDS 182
6.5 CONCLUSION AND OUTLOOK 185
REFERENCES 186
FURTHER READING 190
7 NITROGEN-BEARING LITHIUM COMPOUNDS IN MODERN SYNTHESIS 191
LEONARDO DEGENNARO,
BIAGIA MUSIO, AND RENZO LUISI
7.1 INTRODUCTION 191
7.2 LITHIATION OF CYCLIC AMINES 193
7.2.1 THREE-MEMBERED RINGS: LITHIATED AZIRIDINES 194
7.2.2 FOUR-MEMBERED RINGS: LITHIATED AZETIDINES 200
7.2.3 FIVE-MEMBERED RINGS: LITHIATED PYRROLIDINES 201
7.2.4 SIX-MEMBERED RINGS: LITHIATED PIPERIDINES 210
7.2.5 SEVEN-MEMBERED RINGS: LITHIATED AZEPINES 212
7.2.6 AMINO-ORGANOLITHIUMS FROM HETEROCYCLES WITH MORE THAN ONE
NITROGEN ATOM 212
7.3 LITHIATION OF ACYCLIC AMINES 216
7.4 CONCLUSION AND OUDOOK 220
REFERENCES 221
FURTHER READING 223
8 SULFUR-BEARING LITHIUM COMPOUNDS IN MODERN SYNTHESIS 225
JOS6 LUIS GARCIA
RUANO, ALEJANDRO PARRA, AND JOS6 ALEMDN
8.1 INTRODUCTION 225
8.2 A-LITHIATION 226
8.2.1 THIOETHERS 226
8.2.2 SULFOXIDES 231
8.2.2.1 ALKYL CARBANIONS 231
8.2.2.2 VINYLIC CARBANIONS 234
8.2.3 A-SULFONES 236
8.2.4 A-SULFOXIMINES 240
8.3 P-LITHIATION (ORTHO-DIRECTED LITHIATION) 243
8.3.1 SULFIDES 243
8.3.2 SULFOXIDES 244
8.3.3 SULFONES AND SULFONAMIDES 248
8.3.4 SULFOXIMINES 248
8.4 Y-LITHIATION 249
8.4.1 LATERAL LITHIATION 250
8.4.1.1 SULFOXIDES 250
CONTENTS I XI
8.4.1.2 OTHER ARYL THIODERIVATIVES 260
8.4.2 NITROGENATED FRAGMENTS 261
8.5 CONCLUSION AND OUTLOOK 262
REFERENCES 262
FURTHER READING 270
9 PHOSPHORUS-BEARING LITHIUM COMPOUNDS IN MODERN SYNTHESIS 271
FERNANDO L6PEZ
ORTIZ
9.1 INTRODUCTION 271
9.2 CARBANIONS DIRECTLY LINKED TO A PHOSPHORUS ATOM: PCJ LI 272
9.2.1 PC]LI SPECIES VIA C
A
-LITHIATION OF P(III) COMPOUNDS 272
9.2.2 PCJ
LI SPECIES VIA C
A
-LITHIATION OF P(V) COMPOUNDS 275
9.2.3 PC!
LI SPECIES VIA REACTIONS OF A, P-UNSATURATED P(V)
COMPOUNDS 283
9.3 CARBANIONS SEPARATED BY ONE ATOM FROM THE PHOSPHORUS:
PC
2
LI 284
9.3.1 PC
2
LI SPECIES VIA XC*-LITHIATION (X = N, O) OF P(V) COMPOUNDS 284
9.3.2 PC
2
LI SPECIES VIA ORTHO-LITHIATION OF ORGANOPHOSPHORUS
COMPOUNDS 287
9.4 CARBANIONS SEPARATED BY THREE BONDS FROM A PHOSPHORUS ATOM:
PCJLI 292
9.5 CONCLUSION AND OUTLOOK 293
REFERENCES 293
FURTHER READING 295
10 ADVANCES IN THE CHEMISTRY OF CHIRAL LITHIUM AMIDES 297
ANNE HARRISON-MARCHAND AND JACQUES MADDALUNO
10.1 INTRODUCTION 297
10.2 CHIRAL LITHIUM AMIDES AS BASES 297
10.2.1 ENANTIOSELECTIVE CONVERSION OF EPOXIDES INTO ALLYLIC ALCOHOLS 298
10.2.2 ENANTIOSELECTIVE DEPROTONATION OF CYCLIC PROCHIRAL KETONES 303
10.2.3 ENANTIOSELECTIVE DEPROTONATION OF BRIDGEHEAD CARBONS 307
10.2.4 ENANTIOSELECTIVE DEPROTONATION OF BENZYLIC POSITIONS 310
10.2.5 OTHER REACTIONS 311
10.3 CHIRAL LITHIUM AMIDES AS NUCLEOPHILES 312
10.4 CHIRAL LITHIUM AMIDES AS LIGANDS 315
10.5 CHIRAL LITHIUM AMIDES STRUCTURES 318
10.6 CONCLUSION AND OUTLOOK 324
REFERENCES 325
11 ADVANCES IN CARBOLITHIATION 329
YURY MINKO AND ILAN MAREK
11.1 INTRODUCTION: THE DEFINITION OF THE CARBOLITHIATION REACTION 329
11.2 INTERMOLECULAR CARBOLITHIATION OF ALKENES 330
11.3 INTRAMOLECULAR CARBOLITHIATION OF ALKENES 338
XIII CONTENTS
11.4 INTERMOLECULAR CARBOLITHIATION OF ALKYNES 342
11.5 INTRAMOLECULAR CARBOLITHIATION OF ALKYNES 345
11.6 CONCLUSION AND OUTLOOK 347
REFERENCES 348
FURTHER READING 350
12 REDUCTIVE LITHIATION AND MULTILITHIATED COMPOUNDS IN SYNTHESIS 351
UGO AZZENA AND LUISA PISANO
12.1 INTRODUCTION 351
12.2 ALTERNATIVE SOLVENTS FOR REDUCTIVE LITHIATION REACTIONS 352
12.3 REDUCTIVE LITHIATION OF HETEROCYCLIC COMPOUNDS 354
12.4 REDUCTIVE LITHIATION VIA C-C BOND CLEAVAGE 357
12.5 AMMONIA-FREE BIRCH REDUCTIONS 365
12.6 SILYL-LITHIUM DERIVATIVES 368
REFERENCES 371
FURTHER READING 373
13 DEAROMATIZATION AND ARYL MIGRATION IN ORGANOLITHIUM CHEMISTRY 375
JONATHAN CLAYDEN
13.1 INTRODUCTION 375
13.2 INTERMOLECULAR DEAROMATIZING ADDITION REACTIONS 375
13.3 INTRAMOLECULAR DEAROMATIZING CYCLIZATION REACTIONS 377
13.3.1 ADDITIONS TO ARYLOXAZOLINES 377
13.3.2 ADDITIONS TO ARYLSULFONES 378
13.3.3 ADDITIONS TO AROMATIC SULFONAMIDES AND
PHOSPHONAMIDES 379
13.3.4 ADDITIONS TO AROMATIC AMIDES 381
13.3.5 "PERICYCLIC" DEAROMATIZATIONS 385
13.4 ARYL MIGRATIONS 386
13.4.1 ARYL MIGRATION IN N-ARYL UREAS 386
13.4.2 ARYL MIGRATION IN N-ARYL CARBAMATES 389
13.4.3 ARYL MIGRATION IN N-ARYL THIOCARBAMATES 390
13.5 ALKENYL MIGRATIONS 393
13.6 CONCLUSION AND OUTLOOK 394
REFERENCES 394
14 LITHIUM-BORON CHEMISTRY: A SYNERGISTIC STRATEGY IN MODERN
SYNTHESIS 397
CHARLOTTE C. WATSON, PHILLIP J. UNSWORTH, DANIELE LEONORI, AND
VARINDER K. AGGARWAL
14.1 REAGENT-CONTROLLED LITHIATION-BORYLATION 397
14.2 A-HALOGEN-STABILIZED LITHIUM CARBENOIDS 399
14.3 ALKYLIDENE-TYPE CARBENOIDS 400
14.4 A-OXYGEN-STABILIZED ORGANOLITHIUMS 401
14.4.1 A-LITHIATED PRIMARY CARBAMATES 402
CONTENTS XIII
14.4.2 A-LITHIATED BENZOATE ESTERS 409
14.4.3 A-LITHIATED BENZYLIC CARBAMATES 409
14.4.4 A-LITHIATED ALLYLIC CARBAMATES 415
14.4.5 A-LITHIATED EPOXIDES 415
14.5 A-NITROGEN-STABILIZED ORGANOLITHIUMS 418
14.5.1 A-LITHIATED AZIRIDINES 418
14.6 CONCLUSION AND OUTLOOK 420
REFERENCES 421
FURTHER READING .422
15 LITHIATED AZA-HETEROCYCLES IN MODERN SYNTHESIS 423
YVES FORT
AND CORINNE COMOY
15.1 INTRODUCTION 423
15.2 DIRECT METALLATION WITH LITHIATED BASES VERSUS NUCLEOPHILIC
ADDITION
TO BARE PYRIDINES AND ANALOGS 424
15.3 METALLATION OF DIPOLAR ADDUCTS OF PYRIDINES (N OXIDES OR BF
3
ADDUCTS) 429
15.4 HALOGEN-METAL EXCHANGE IN AZA-HETEROCYDIC SERIES 430
15.5 DIRECTED ORTHO-METALLATION (DOM) OF AZA-HETEROCYCLES 432
15.6 HALOGEN DANCE: A USEFUL SIDE REACTION 435
15.7 LATERAL AND REMOTE METALLATIONS 437
15.8 LITHIATION INVESTIGATIONS OF THE NICOTINIC UNIT 440
15.9 MISCELLANEOUS EXAMPLES OF VARIOUS HETEROARYLLITHIUM REAGENTS AS
KEY INTERMEDIATES IN ORGANIC SYNTHESIS 445
15.10 CONCLUSION AND OUTLOOK 452
REFERENCES 453
16 LITHIUM COMPOUNDS IN CROSS-COUPLING REACTIONS 463
MASAKI SHIMIZU
16.1 INTRODUCTION 463
16.2 CROSS-COUPLING REACTIONS OF ORGANOLITHIUM REAGENTS 464
16.3 CROSS-COUPLING REACTIONS OF LITHIUM ENOLATES 474
16.4 CROSS-COUPLING REACTIONS OF LITHIUM AMIDES 481
16.5 CROSS-COUPLING REACTIONS OF LITHIUM THIOLATES 484
16.6 CONCLUSION AND OUTLOOK 486
REFERENCES 488
17 MICROREACTOR TECHNOLOGY IN LITHIUM CHEMISTRY 491
AIICHIRO NAGAKI AND JUN-ICHI YOSHIDA
17.1 INTRODUCTION 491
17.2 CHARACTERISTIC FEATURES OF FLOW MICROREACTORS 492
17.3 CONTROL OF UNSTABLE ORGANOLITHIUMS USING FLOW MICROREACTORS 493
17.4 PROTECTING-GROUP-FREE SYNTHESIS USING FLOW MICROREACTORS 497
17.5 STEREOSELECTIVE REACTIONS BASED ON CONTROL OF CONFIGURATIONALLY
UNSTABLE ORGANOLLITHIUMS USING FLOW MICROREACTORS 499
XIV
| CONTENTS
17.6 SWITCHING REACTION PATHWAYS OF ORGANOLITHIUMS USING FLOW
MICROREACTORS 499
17.7 REACTION INTEGRATION USING FLOW MICROREACTORS 501
17.8 CONTROLLED/LIVING ANIONIC POLYMERIZATION OF VINYL MONOMERS USING
ORGANOLITHIUM INITIATORS IN FLOW MICROREACTORS 503
17.8.1 CONTROLLED/ LIVING ANIONIC POLYMERIZATION OF STYRENES 503
17.8.2 CONTROLLED/LIVING ANIONIC POLYMERIZATION OF ALKYL METHACRYLATES
USING FLOW MICROREACTORS 506
17.8.3 CONTROLLED/LIVING ANIONIC BLOCK COPOLYMERIZATION OF STYRENES AND
ALKYL METHACRYLATES USING INTEGRATED FLOW MICROREACTORS 508
17.8.4 CONTROLLED/LIVING ANIONIC POLYMERIZATION OF FERT-BUTYL ACRYLATES
USING FLOW MICROREACTORS 509
17.9 CONCLUSION AND OUTLOOK 509
REFERENCES 510
18 PRACTICAL ASPECTS OF ORGANOLITHIUM CHEMISTRY 513
LEONARDO DEGENNARO, ARIANNA GIOVINE, LAURA CARROCCIA, AND RENZO LUISI
18.1 INTRODUCTION 513
18.2 GENERAL PREPARATIONS OF ORGANOLITHIUM COMPOUNDS 514
18.2.1 REDUCTION WITH LITHIUM METAL 514
18.2.2 EXCHANGE REACTION FROM HALIDES OR ORGANOMETALLICS
(TRANSMETALATION) 515
18.2.3 METALATIONBY H/LI PERMUTATION (DEPROTONATION) 516
18.2.4 ADDITION OF ORGANOLITHIUMS TO UNSATURATED SYSTEMS 517
18.3 PRACTICAL ASPECTS RELATED TO THE USE OF ORGANOLITHIUMS 518
18.3.1 STABILITY AND REACTIVITY OF ORGANOLITHIUMS 518
18.3.2 COMMERCIALLY AVAILABLE ORGANOLITHIUM COMPOUNDS 522
18.3.3 TITRATION OF ORGANOLITHIUMS 523
18.4 NMR ANALYSIS OF ORGANOLITHIUM REAGENTS 530
18.5 HAZARDS ASSOCIATED WITH ORGANOLITHIUM COMPOUNDS 531
18.6 SETTING UP OF EXPERIMENTS USING ORGANOLITHIUMS 532
18.7 TRANSFERRING ORGANOLITHIUMS 533
18.7.1 SYRINGE TECHNIQUE 534
18.7.2 CANNULA TECHNIQUE 535
18.7.3 CONCLUSION AND OUTLOOK 536
REFERENCES 537
FURTHER READING 538
INDEX 539 |
| any_adam_object | 1 |
| author2 | Luisi, Renzo |
| author2_role | edt |
| author2_variant | r l rl |
| author_GND | (DE-588)1051321441 |
| author_facet | Luisi, Renzo |
| building | Verbundindex |
| bvnumber | BV041707332 |
| classification_rvk | VK 5500 VK 7726 |
| classification_tum | CHE 334f CHE 622f CHE 362f CHE 336f CHE 330f |
| ctrlnum | (OCoLC)864595563 (DE-599)DNB1042297428 |
| dewey-full | 547.05381 |
| dewey-hundreds | 500 - Natural sciences and mathematics |
| dewey-ones | 547 - Organic chemistry |
| dewey-raw | 547.05381 |
| dewey-search | 547.05381 |
| dewey-sort | 3547.05381 |
| dewey-tens | 540 - Chemistry and allied sciences |
| discipline | Chemie / Pharmazie Chemie |
| format | Book |
| fullrecord | <?xml version="1.0" encoding="UTF-8"?><collection xmlns="http://www.loc.gov/MARC21/slim"><record><leader>00000nam a22000008c 4500</leader><controlfield tag="001">BV041707332</controlfield><controlfield tag="003">DE-604</controlfield><controlfield tag="005">20160216</controlfield><controlfield tag="007">t</controlfield><controlfield tag="008">140226s2014 gw ad|| |||| 00||| eng d</controlfield><datafield tag="015" ind1=" " ind2=" "><subfield code="a">13,N40</subfield><subfield code="2">dnb</subfield></datafield><datafield tag="016" ind1="7" ind2=" "><subfield code="a">1042297428</subfield><subfield code="2">DE-101</subfield></datafield><datafield tag="020" ind1=" " ind2=" "><subfield code="a">3527333436</subfield><subfield code="9">3-527-33343-6</subfield></datafield><datafield tag="020" ind1=" " ind2=" "><subfield code="a">9783527333431</subfield><subfield code="c">Gb. : ca. EUR 149.00 (DE) (freier Pr.), ca. 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| genre | (DE-588)4143413-4 Aufsatzsammlung gnd-content |
| genre_facet | Aufsatzsammlung |
| id | DE-604.BV041707332 |
| illustrated | Illustrated |
| indexdate | 2024-08-03T01:18:08Z |
| institution | BVB |
| isbn | 3527333436 9783527333431 9783527667512 |
| language | English |
| oai_aleph_id | oai:aleph.bib-bvb.de:BVB01-027154598 |
| oclc_num | 864595563 |
| open_access_boolean | |
| owner | DE-91S DE-BY-TUM DE-11 DE-29T DE-703 DE-19 DE-BY-UBM |
| owner_facet | DE-91S DE-BY-TUM DE-11 DE-29T DE-703 DE-19 DE-BY-UBM |
| physical | XXIV, 545 S. Ill., graph. Darst. 244 mm x 170 mm |
| publishDate | 2014 |
| publishDateSearch | 2014 |
| publishDateSort | 2014 |
| publisher | Wiley-VCH |
| record_format | marc |
| spelling | Lithium compounds in organic synthesis from fundamentals to applications ed. by Renzo Luisi ... 201403 Weinheim Wiley-VCH 2014 XXIV, 545 S. Ill., graph. Darst. 244 mm x 170 mm txt rdacontent n rdamedia nc rdacarrier Katalyse (DE-588)4029921-1 gnd rswk-swf Organische Synthese (DE-588)4075695-6 gnd rswk-swf Lithiumverbindungen (DE-588)4322206-7 gnd rswk-swf Lithiumorganische Verbindungen (DE-588)4132581-3 gnd rswk-swf (DE-588)4143413-4 Aufsatzsammlung gnd-content Organische Synthese (DE-588)4075695-6 s Lithiumverbindungen (DE-588)4322206-7 s Katalyse (DE-588)4029921-1 s DE-604 Lithiumorganische Verbindungen (DE-588)4132581-3 s b DE-604 Luisi, Renzo (DE-588)1051321441 edt Erscheint auch als Online-Ausgabe, EPUB 978-3-527-66753-6 Erscheint auch als Online-Ausgabe, MOBI 978-3-527-66752-9 Erscheint auch als Online-Ausgabe, PDF 978-3-527-66754-3 X:MVB text/html http://deposit.dnb.de/cgi-bin/dokserv?id=4462460&prov=M&dok_var=1&dok_ext=htm Inhaltstext DNB Datenaustausch application/pdf http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=027154598&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA Inhaltsverzeichnis |
| spellingShingle | Lithium compounds in organic synthesis from fundamentals to applications Katalyse (DE-588)4029921-1 gnd Organische Synthese (DE-588)4075695-6 gnd Lithiumverbindungen (DE-588)4322206-7 gnd Lithiumorganische Verbindungen (DE-588)4132581-3 gnd |
| subject_GND | (DE-588)4029921-1 (DE-588)4075695-6 (DE-588)4322206-7 (DE-588)4132581-3 (DE-588)4143413-4 |
| title | Lithium compounds in organic synthesis from fundamentals to applications |
| title_auth | Lithium compounds in organic synthesis from fundamentals to applications |
| title_exact_search | Lithium compounds in organic synthesis from fundamentals to applications |
| title_full | Lithium compounds in organic synthesis from fundamentals to applications ed. by Renzo Luisi ... |
| title_fullStr | Lithium compounds in organic synthesis from fundamentals to applications ed. by Renzo Luisi ... |
| title_full_unstemmed | Lithium compounds in organic synthesis from fundamentals to applications ed. by Renzo Luisi ... |
| title_short | Lithium compounds in organic synthesis |
| title_sort | lithium compounds in organic synthesis from fundamentals to applications |
| title_sub | from fundamentals to applications |
| topic | Katalyse (DE-588)4029921-1 gnd Organische Synthese (DE-588)4075695-6 gnd Lithiumverbindungen (DE-588)4322206-7 gnd Lithiumorganische Verbindungen (DE-588)4132581-3 gnd |
| topic_facet | Katalyse Organische Synthese Lithiumverbindungen Lithiumorganische Verbindungen Aufsatzsammlung |
| url | http://deposit.dnb.de/cgi-bin/dokserv?id=4462460&prov=M&dok_var=1&dok_ext=htm http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=027154598&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA |
| work_keys_str_mv | AT luisirenzo lithiumcompoundsinorganicsynthesisfromfundamentalstoapplications |