Macrocyclic chemistry: aspects of organic and inorganic supramolecular chemistry
Gespeichert in:
| Hauptverfasser: | , , |
|---|---|
| Format: | Buch |
| Sprache: | English German |
| Veröffentlicht: |
Weinheim [u.a.]
VCH
1993
|
| Schlagworte: | |
| Online-Zugang: | Inhaltsverzeichnis |
| Beschreibung: | Literaturangaben. - Aus d. Franz. übers. |
| Beschreibung: | XV, 384 S. graph. Darst. |
| ISBN: | 3527283307 1560811641 |
Internformat
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Datensatz im Suchindex
| _version_ | 1823026305570963456 |
|---|---|
| adam_text |
B.
DIETRICH,
P.
VIOUT, J.-M. LEHN
MACROCYCLIC CHEMISTRY
ASPECTS OF ORGANIC AND INORGANIC
SUPRAMOLECULAR
CHEMISTRY
\7IF^~WT VFF^
WEINHEIM
YY
NEW YORK
YY
V
/
UE HL BASEL
YY
CAMBRIDGE
CONTENTS
INTRODUCTION XI
NOTE CONCERNING NOMENCLATURE XVII
PART I MACROCYCLE SYNTHESIS
1
CHAPTER 1 SYNTHETIC PRINCIPLES 3
1.1 EFFECT OF CHAIN LENGTH ON CYCLOALKANE FORMATION 4
1.2 EFFECT OF THE NATURE OF THE CHAIN ATOMS AND GROUPS ON RING
FORMATION
8
1.2.1 HETEROATOMS 8
1.2.2 RIGID GROUPS 9
1.2.3 GEM-DIMETHYL SUBSTITUENTS 11
1.3 INFLUENCE OF CYCLIZATION TYPE ON MACROCYCLE FORMATION 12
CHAPTER 2 CYCLIZATION 15
2.1 PRINCIPLES AND CONCEPTS 15
2.2 DIFFUSION CONTROLLED CYCLIZATION 16
2.2.1 INTRAMOLECULAR DONOR-ACCEPTOR INTERACTIONS 16
2.2.2 EXCIMER-EXCIPLEX 19
2.2.3 INTRAMOLECULAR EXCIMERS AND EXCIPLEXES 20
2.2.4 FLUORESCENCE QUENCHING BY INTRAMOLECULAR ENERGY TRANSFER (IN
TERNAL
CONVERSION) 21
2.2.5 FLUORESCENCE QUENCHING BY INTRAMOLECULAR ELECTRON TRANSFER. 23
2.3 CYCLIZATIONS UNDER CONFORMATIONAL CONTROL 24
2.3.1 ELECTRON TRANSFER 24
2.3.2 PHOSPHORESCENCE QUENCHING 26
VIII
CONTENTS
2.4 INTERNAL RING CLOSURE. REMOTE FUNCTIONALIZATION 27
2.4.1 CHROMIC ANHYDRIDE OXIDATIONS 28
2.4.2 PHOTOCHEMICAL FUNCTIONALIZATION BY BENZOPHENONE 30
2.4.3 REMOTE CHLORINATION 33
2.4.4 TEMPORARY ASSOCIATION BETWEEN THE REAGENT AND THE SUBSTRATE . 35
CHAPTER 3 RING CLOSURE METHODS 39
3.1 HIGH DILUTION TECHNIQUE 39
3.1.1 PRINCIPLE 39
3.1.2 IMPLEMENTATION 40
3.2 DEPOLYMERIZATION 42
3.3 TEMPLATED RING CLOSURE 43
3.3.1 PRINCIPLE 43
3.3.2 CYCLIZATION ON ENDO-TEMPLATES 45
3.3.3 CYCLIZATION ON EXTERNAL TEMPLATES: METALLOIDS 53
3.3.4 CYCLIZATION ON EXTERNAL TEMPLATES: METAL CATIONS 60
3.3.5 TEMPLATE REAGENTS. CYCLOOLEFIN METATHESIS 75
3.4 SELF-ASSEMBLY OF RIGID UNITS 77
3.4.1 PORPHYRIN SYNTHESIS 77
3.4.2 THIAPORPHYRINS 77
3.4.3 TETRAHETEROCYCLIC COMPOUNDS SIMILAR TO PORPHYRINS 80
3.4.4 PHENOL-ALDEHYDE MACROCYCLES 82
3.5 CROWN ETHER MACROCYCLIC COMPOUNDS 94
3.5.1 GENERAL SYNTHETIC METHODS 94
3.5.2 INTRODUCTION OF CYCLIC SUBUNITS 98
3.5.3 INTRODUCTION OF CHIRAL SUBUNITS 99
3.5.4 CATIONIC CYCLOOLIGOMERIZATION OF ETHYLENE OXIDE 104
3.5.5 CYCLIZATION USING TEMPLATES 108
3.6 MACROCYCLIC LACTONES - MACROLIDES 112
3.6.1 GENERAL METHODS OF MACROLACTONIZATION 112
3.6.2 CUE-HALOCARBOXYLATE CYCLIZATION 113
3.6.3 CYCLIZATION OF CO-HYDROXY ACIDS 118
3.6.4 VARIOUS METHODS OF MACROLACTONIZATION 134
3.6.5 MACROLACTONIZATION VIA CARBON-CARBON-BOND FORMATION 140
3.6.6
LACTONIZATION OF VERY COMPLEX SYSTEMS. THIOLACTONES 143
3.7 MACROCYCLIC LACTAMS 146
3.7.1 MACROCYCLIC SPERMIDINE ALKALOIDS 146
3.7.2 FORMATION OF THE LACTAM GROUP IN RIFAMYCIN 149
3.7.3 LACTAM SYNTHESIS USING DIAZASILOLIDINES 151
3.7.4 CYCLOPEPTIDES 152
3.8 MACROCARBOCYCLES 152
REFERENCES FOR PART I 157
CONTENTS
IX
PART II MACROCYCLIC COMPLEXES
-
CRYPTATES
167
INTRODUCTION 169
CHAPTER 1 SYNTHETIC MACROCYCLIC COMPLEXES 171
1.1 COMPLEMENTARITY OF THE CAVITY AND CATION 171
1.1.1 CONFORMATION OF THE MACROCYCLE 171
1.1.2 RELATIVE SIZES OF THE CATION AND THE CAVITY 173
1.2 EFFECT OF THE ANION 179
1.3 PARTICIPATION OF WATER MOLECULES. SIMULTANEOUS COMPLEXATION
OF
A CATION AND WATER 182
1.4 LATERAL INTERACTIONS 185
1.5 FORMATION OF A SECOND COORDINATION SPHERE 190
1.6 MISCELLANEOUS COMPLEXES 193
1.7 COMPLEXATION SITES OTHER THAN OXYGEN 195
1.7.1 AZAOXA MACROCYCLES 195
1.7.2 OXATHIA MACROCYCLES 198
CHAPTER 2 NATURAL MACROCYCLIC IONOPHORES 203
2.1 INTRODUCTION 203
2.2 STRUCTURAL ELEMENTS 204
2.2.1 PEPTIDES 204
2.2.2 DEPSIPEPTIDES AND DEPSIDES 205
2.3 CYCLODEPSIPEPTIDES AND THEIR COMPLEXES 206
2.3.1 VALINOMYCIN 207
2.3.2 BEAUVERICIN. ENNIATINS A AND B 213
2.4 CYCLOPEPTIDES 215
2.4.1 ANTAMANIDE 216
2.4.2 GRAMICIDIN S 219
2.4.3 SYNTHETIC CYCLOPEPTIDES 220
2.5 THE DEPSIDES AND THEIR METAL COMPLEXES 227
2.5.1 NACTINS 227
2.5.2 SYNTHETIC NACTIN ANALOGS 231
2.6 TRANSMEMBRANE MOLECULAR CHANNELS 233
2.6.1 THE GRAMICIDINS 234
2.6.2 ALAMETHICIN AND SUZUKACILLIN 235
2.6.3 A SYNTHETIC CHANNEL 239
X
CONTENTS
CHAPTER 3 MACROBICYCLIC LIGANDS. CRYPTANDS 241
3.1 INTRODUCTION 241
3.1.1 GENERAL POINTS 241
3.1.2 NATURE OF THE BRIDGEHEADS 243
3.2 SYNTHETIC STRATEGIES 244
3.2.1 STEPWISE SYNTHESIS 244
3.2.2 CONDENSATION OF TWO TRIPODES 263
3.2.3 VARIANT OF THE CONDENSATION OF TWO TRIPODES (TRIPODE
CAPPING)
268
3.2.4 CYCLIZATIONS USING AN INTERNAL TEMPLATE 271
3.2.5 CYCLIZATIONS USING AN EXTERNAL TEMPLATE 275
3.2.6 MISCELLANEOUS 286
3.3 MACROCYCLIC AND MACROBICYCLIC COMPLEXES. CRYPTATES 289
3.3.1 PROTON TRANSFER 289
3.3.2 PROTON TRANSFER IN PROTON CRYPTATES 300
3.3.3 METAL CRYPTATES. MACROBICYCLIC INCLUSION COMPLEXES 312
3.3.4 STABILITY AND SELECTIVITY OF MACROCYCLIC COMPLEXES 316
3.3.5 STABILITY AND SELECTIVITY OF CRYPTATES (MACROBICYCLIC COMPLEXES)
342
REFERENCES FOR PART II 357
ILLUSTRATION ACKNOWLEDGEMENTS 371
INDEX 375 |
| any_adam_object | 1 |
| author | Dietrich, Bernard Viout, Paulette Lehn, Jean-Marie 1939- |
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| bvnumber | BV025861391 |
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| isbn | 3527283307 1560811641 |
| language | English German |
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| physical | XV, 384 S. graph. Darst. |
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| spelling | Dietrich, Bernard Verfasser aut Aspects de la chimie des composés macrocycliques Macrocyclic chemistry aspects of organic and inorganic supramolecular chemistry B. Dietrich ; P. Viout ; J.-M. Lehn. [Transl.: William E. Douglas] Weinheim [u.a.] VCH 1993 XV, 384 S. graph. Darst. txt rdacontent n rdamedia nc rdacarrier Literaturangaben. - Aus d. Franz. übers. Komplexe (DE-588)4133953-8 gnd rswk-swf Supramolekulare Struktur (DE-588)4208977-3 gnd rswk-swf Makrocyclische Verbindungen (DE-588)4168678-0 gnd rswk-swf Supramolekulare Chemie (DE-588)4306141-2 gnd rswk-swf Makrocyclische Verbindungen (DE-588)4168678-0 s DE-604 Supramolekulare Chemie (DE-588)4306141-2 s Supramolekulare Struktur (DE-588)4208977-3 s 1\p DE-604 Komplexe (DE-588)4133953-8 s 2\p DE-604 Viout, Paulette Verfasser aut Lehn, Jean-Marie 1939- Verfasser (DE-588)113097336 aut DNB Datenaustausch application/pdf http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=019109062&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA Inhaltsverzeichnis 1\p cgwrk 20201028 DE-101 https://d-nb.info/provenance/plan#cgwrk 2\p cgwrk 20201028 DE-101 https://d-nb.info/provenance/plan#cgwrk |
| spellingShingle | Dietrich, Bernard Viout, Paulette Lehn, Jean-Marie 1939- Macrocyclic chemistry aspects of organic and inorganic supramolecular chemistry Komplexe (DE-588)4133953-8 gnd Supramolekulare Struktur (DE-588)4208977-3 gnd Makrocyclische Verbindungen (DE-588)4168678-0 gnd Supramolekulare Chemie (DE-588)4306141-2 gnd |
| subject_GND | (DE-588)4133953-8 (DE-588)4208977-3 (DE-588)4168678-0 (DE-588)4306141-2 |
| title | Macrocyclic chemistry aspects of organic and inorganic supramolecular chemistry |
| title_alt | Aspects de la chimie des composés macrocycliques |
| title_auth | Macrocyclic chemistry aspects of organic and inorganic supramolecular chemistry |
| title_exact_search | Macrocyclic chemistry aspects of organic and inorganic supramolecular chemistry |
| title_full | Macrocyclic chemistry aspects of organic and inorganic supramolecular chemistry B. Dietrich ; P. Viout ; J.-M. Lehn. [Transl.: William E. Douglas] |
| title_fullStr | Macrocyclic chemistry aspects of organic and inorganic supramolecular chemistry B. Dietrich ; P. Viout ; J.-M. Lehn. [Transl.: William E. Douglas] |
| title_full_unstemmed | Macrocyclic chemistry aspects of organic and inorganic supramolecular chemistry B. Dietrich ; P. Viout ; J.-M. Lehn. [Transl.: William E. Douglas] |
| title_short | Macrocyclic chemistry |
| title_sort | macrocyclic chemistry aspects of organic and inorganic supramolecular chemistry |
| title_sub | aspects of organic and inorganic supramolecular chemistry |
| topic | Komplexe (DE-588)4133953-8 gnd Supramolekulare Struktur (DE-588)4208977-3 gnd Makrocyclische Verbindungen (DE-588)4168678-0 gnd Supramolekulare Chemie (DE-588)4306141-2 gnd |
| topic_facet | Komplexe Supramolekulare Struktur Makrocyclische Verbindungen Supramolekulare Chemie |
| url | http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=019109062&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA |
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