Acetylene chemistry: chemistry, biology, and material science
Gespeichert in:
| Format: | Buch |
|---|---|
| Sprache: | English |
| Veröffentlicht: |
Weinheim
WILEY-VCH
2005
|
| Schlagworte: | |
| Online-Zugang: | Inhaltsverzeichnis |
| Beschreibung: | XX, 508 S. zahlr. graph. Darst. 25 cm |
| ISBN: | 3527307818 |
Internformat
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| 245 | 1 | 0 | |a Acetylene chemistry |b chemistry, biology, and material science |c ed. by F. Diederich ... |
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Datensatz im Suchindex
| _version_ | 1804133041387339776 |
|---|---|
| adam_text | ACETYLENE CHEMISTRY CHEMISTRY, BIOLOGY AND MATERIAL SCIENCE EDITED BY F.
DIEDERICH, P.J. STANG, R. R. TYKWINSKI WILEY- VCH WILEY-VCH VERLAG GMBH
& CO. KGAA / CONTENTS 1 THEORETICAL STUDIES ON ACETYLENIC SCAFFOLDS 1
1.1 INTRODUCTION 1 1.2 LINEAR ACETYLENIC SCAFFOLDS 2 1.2.1 THE DICARBON
MOLECULE AND ACETYLENE 2 1.2.2 UNCAPPED PURE SP CARBON CHAINS 3 1.2.3
CAPPED AU-SP OLIGOACETYLENIC CHAINS 5 1.2.4 HYBRID SP-SP 2
OLIGOACETYLENIC MOLECULES 9 1.2.5 HYBRID SP-SP 1 OLIGOACETYLENIC
MOLECULES 14 1.3 CYCLIC ACETYLENIC SCAFFOLDS 15 1.3.1 HYBRID SP-SP }
RINGS 15 1.3.2 HYBRID SP-SP 2 RINGS (DEHYDROANNULENES) 20 1.3.3
CORBO-HETEROANNULENES 32 1.4 STAR-SHAPED ACETYLENIC SCAFFOLDS 34 1.4.1
ATOMIC CORES 34 1.4.2 ROD CORES 34 1.4.3 CYCLIC CORES 37 1.5 CAGE
ACETYLENIC SCAFFOLDS 40 1.6 CONCLUSION 41 ACKNOWLEDGEMENTS 42 2
SYNTHESIS OF HETEROCYCLES AND CARBOCYCLES BY ELECTROPHILIC CYCLIZATION
OF ALKYNES 51 2.1 INTRODUCTION 51 2.2 CYCLIZATION OF OXYGEN COMPOUNDS 51
2.2.1 CYCLIZATION OF ACETYLENIC ALCOHOLS 51 2.2.2 CYCLIZATION OF
ACETYLENIC PHENOLS 55 2.2.3 CYCLIZATION OF ACETYLENIC ETHERS 57 2.2.4
CYCLIZATION OF ACETYLENIC ACIDS AND DERIVATIVES 59 2.2.5 CYCLIZATION OF
ACETYLENIC ALDEHYDES AND KETONES 63 2.3 CYCLIZATION OF SULFUR AND
SELENIUM COMPOUNDS 66 2.4 CYCLIZATION OF NITROGEN COMPOUNDS 67 2.4.1
CYCLIZATION OF ACETYLENIC AMINES 67 2.4.2 CYCLIZATION OF ACETYLENIC
AMIDES 70 ACETYLENE CHEMISTRY. CHEMISTRY, BIOLOGY AND MATERIAL SCIENCE.
EDITED BY F. DIEDERICH, P. J. STANG, R. R. TYKWINSKI COPYRIGHT 2005
WILEY-VCH VERLAG GMBH & CO. KGAA, WEINHEIM ISBN 3-527-30781-8 VIII
CONTENTS 2.4.3 CYCLIZATION OF ACETYLENIC CARBAMATES 73 2.4.4 CYCLIZATION
OF ACETYLENIC SULFONAMIDES 75 2.4.5 CYCLIZATION OF ACETYLENIC ENAEMINES
AND IMINES 77 2.4.6 CYCLIZATION OF OTHER ACETYLENIC NITROGEN FUNCTIONAL
GROUPS 79 2.5 CYCLIZATION OF CARBON ONTO ACETYLENES 81 2.5.1 CYCLIZATION
OF ACETYLENIC CARBONYL COMPOUNDS AND DERIVATIVES 81 2.5.2 CYCLIZATION OF
DIACETYLENES 83 2.5.3 CYCLIZATION OF ARYL ACETYLENES 84 2.5.4
CYCLIZATION OF ACETYLENIC ORGANOMETALLICS 89 2.6 CONCLUSIONS 90 2.7
REPRESENTATIVE EXPERIMENTAL PROCEDURES 90 2.7.1 SYNTHESIS OF
A-METHYLENE-Y-BUTYROLACTONES BY CARBONYLATION OF L-ALKYN-4-OLS 90 2.7.2
SYNTHESIS OF 1-ALKOXYISOCHROMENES BY CYCLIZATION OF
2-(L-ALKYNYL)BENZALDEHYDES 90 2.7.3 SYNTHESIS OF 3-ARYL(VINYLIC)INDOLES
BY PALLADIUM-CATALYZED CROSS-COUPLING OF ARYL HALIDES OR VINYLIC
TRIFLATES AND 2-(L-ALKYNYL)TRIFLUOROACETANILIDES 90 2.7.4 SYNTHESIS OF
PYRIDINES BY THE GOLD-CATALYZED CROSS-COUPLING OF KETONES AND PROPARGYL
AMINE 91 2.7.5 SYNTHESIS OF 4-IODOISOQUINOLINES BY THE CYCLIZATION OF
IMINOALKYNES 91 2.7.6 SYNTHESIS OF CYCLIC AMINES BY ACETYLENE-IMINIUM
ION CYCLIZATIONS 91 ACKNOWLEDGEMENTS 92 3 ADDITION OF TERMINAL
ACETYLIDES TO CO AND CN ELECTROPHILES 101 3.1 INTRODUCTION 101 3.2
BACKGROUND 103 3.3 ADDITIONS WITH STOICHIOMETRIC AMOUNTS OF METAL
ACETYLIDES 106 3.4 NUCLEOPHILIC CO ADDITIONS INVOLVING THE USE OF ZN(N)
SALTS 114 3.5 ACETYLENE ADDITIONS TO CN ELECTROPHILES 125 3.6 CONCLUSION
131 3.7 EXPERIMENTAL PROCEDURES 131 3.7.1 GENERAL PROCEDURE FOR THE
ENANTIOSELECTIVE ALKYNYLATION OF ALDEHYDES BY THE USE OF STOICHIOMETRIC
AMOUNTS OF ZN(OTF) 2 131 3.7.2 GENERAL PROCEDURE FOR THE ZN(OTF) 2
-CATALYZED ENANTIOSELECTIVE ALKYNYLATION OF ALDEHYDES 132 3.7.3 GENERAL
PROCEDURE FOR THE ENANTIOSELECTIVE ALKYNYLATION OF KETONES CATALYZED BY
ZN(SALEN) COMPLEXES 132 3.7.4 GENERAL PROCEDURE FOR THE ZN(OTF) 2
-CATALYZED DIASTEREOSELECTIVE ALKYNYLATION OF N-GLYCOSYL NITRONES 133
3.7.5 GENERAL PROCEDURE FOR THE ET 2 ZN-CATALYZED DIASTEREOSELECTIVE
ALKYNYLATION OF CHIRAL NITRONES 133 3.7.6 GENERAL PROCEDURE FOR THE
CUBR-CATALYZED ENANTIOSELECTIVE PREPARATION OF PROPARGYLAMINES 133 3.7.7
GENERAL PROCEDURE FOR THE [IRCL(COD)] 2 -CATALYZED ALKYNYLATION OF
IMINES 134 I CONTENTS IX 4 TRANSITION METAL ACETYLIDES 139 4.1
INTRODUCTION 139 4.2 GENERAL COMMENTS 140 4.2.1 STRUCTURE AND BONDING
140 4.2.2 SYNTHESES 141 4.2.3 REACTIONS 144 4.3 TITANOCENE- AND
ZIRCONOCENE-ACETYLIDES 146 4.3.1 MCCR 246 4.3.2 M(CCR) 2 148 4.3.3
M(CCR) 3 148 4.3.4 PRODUCTS OF [CP 2 M(N 2 -RC 2 R)] AND [CP* 2 M(TI 2
-RC 2 R)] WITH ACETYLENES 149 4.3.5 REACTIONS 151 4.4 COMPLEXATION OF
MCCM 260 4.4.1 EXAMPLES 260 4.4.2 MOLECULAR DYNAMICS OF ACETYLIDES 262
4.4.3 ACETYLIDES IN THE TOPOMERIZATION OF ALKYNES 263 4.5 SUMMARY AND
OUTLOOK 265 4.6 TYPICAL EXPERIMENTAL PROCEDURES 266 4.6.1 SYNTHESIS OF A
MONOMERIC TI(IN) MONOACETYLIDE [CP* 2 TICC BU] 266 4.6.2 SYNTHESIS OF A
TI(M) BISACETYLIDE TWEEZER [CP2TI(CC BU) 2 ][LI(THF)] 266 4.6.3
SYNTHESIS OF A DINUCLEAR TI(IN) MONOACETYLIDE [CP 2 TIC 2 SIME3)] 2 BY
CC CLEAVAGE OF A 1,3-BUTADIYNE 267 4.6.4 SYNTHESIS OFA ZR(IV)
BISACETYLIDE [CP* 2 ZR(CCSIME 3 ) 2 ] 267 4.6.5 SYNTHESIS OF A
ZIRCONACYCLOCUMULENE [CP* 2 ZR(TI 4 -L,2,3,4-ME3SIC 4 SIME3)] 267
ACKNOWLEDGMENTS 268 5 ACETYLENOSACCHARIDES 273 5.1 INTRODUCTION 273 5.2
ISOLATION OF ACETYLENOSACCHARIDES FROM NATURAL SOURCES 274 5.3
PREPARATION OF MONOALKYNYLATED ACETYLENOSACCHARIDES 277 5.3.1
PREPARATION OF LINEAR ACETYLENOSACCHARIDES 277 5.3.2 PREPARATION OF
BRANCHED-CHAIN ACETYLENOSACCHARIDES 288 5.4 PREPARATION OF DIALKYNYLATED
ACETYLENOSACCHARIDES 293 5.4.1 LINEAR DIALKYNYLATED ACETYLENOSACCHARIDES
293 5.4.2 BRANCHED DIALKYNYLATED ACETYLENOSACCHARIDES 294 5.4.2.1
4-O-ALKYNYL-SS-D-GLUCOPYRANOSYLACETYLENES 295 5.5 TRANSFORMATIONS OF
ACETYLENOSACCHARIDES 203 5.5.1 RING-FORMING REACTIONS 204 5.5.2 COUPLING
REACTIONS 222 5.5.2.1 HOMOCOUPLING OF ACETYLENOSACCHARIDES 223 5.6
BIOLOGICAL AND MEDICINAL USES OF ACETYLENOSACCHARIDES 225 5.7
EXPERIMENTAL PROTOCOLS 225 ACKNOWLEDGEMENTS 229 CONTENTS 6
SEMICONDUCTING POLY(ARYLENE ETHYLENEJS 233 6.1 INTRODUCTION 233 6.2
SYNTHESIS 234 6.3 CONDUCTING PROPERTIES OF PARES 236 6.4 PHOTOPHYSICAL
PROPERTIES AND INTERPOLYMER ELECTRONIC INTERACTIONS 6.5 SENSOR
APPLICATIONS 247 6.6 SUPERSTRUCTURES 249 6.7 SUMMARY 255 6.8 GENERAL
PROCEDURES FOR SYNTHESIS OF PPES 255 ACKNOWLEDGEMENTS 256 7 POLYYNES VIA
ALKYLIDENE CARBENES AND CARBENOIDS 259 7.1 INTRODUCTION 259 7.2
ALKYLIDENE CARBENE AND CARBENOID SPECIES 260 7.3 ALKYNE FORMATION FROM
CARBENES AND CARBENOIDS 262 7.3.1 SYNTHESIS OF ACETYLENES: THE
FRITSCH-BUTTENBERG-WIECHELL REARRANGEMENT 261 7.3.2 SYNTHESIS OF
1,3-BUTADIYNES 265 7.3.3 SYNTHESIS OF 1,3,5-HEXATRIYNES 26S 7.3.4 TRI-
AND PENTAYNES FROM FREE ALKYLIDENE CARBENES 273 7.4 TOWARD APPLICATIONS
274 7.4.1 NATURAL PRODUCTS SYNTHESIS 274 7.4.2 EXTENDED ARYLENETHYNYLENE
DERIVATIVES 276 7.4.3 CYCLO[N]CARBONS 283 7.5 LINEAR CONJUGATED POLYYNES
284 7.5.1 SYNTHESIS OF TRIISOPROPYLSILYL END-CAPPED POLYYNES 285 7.5.2
SOLID-STATE CHARACTERIZATION 289 7.5.3 LINEAR OPTICAL PROPERTIES 291
7.5.4 THIRD-ORDER NONLINEAR OPTICAL PROPERTIES 294 7.6 CONCLUSIONS 296
7.7 EXPERIMENTAL PROCEDURES 297 7.7.1 GENERAL PROCEDURE FOR
FRIEDEL-CRAFTS ACYLATION 297 7.7.2 GENERAL PROCEDURE FOR
DIBROMOOLEFINATION 297 7.7.3 GENERAL FBW REARRANGEMENT PROCEDURE 297
7.7.4 GENERAL OXIDATIVE COUPLING PROCEDURE 298 ACKNOWLEDGEMENTS 298 8
MACROCYCLES BASED ON PHENYLACETYLENE SCAFFBLDING 303 8.1 INTRODUCTION
303 8.2 SYNTHETIC STRATEGIES 304 8.2.1 INTERMOLECULAR APPROACH 304 8.2.2
INTRAMOLECULAR APPROACH 307 8.2.3 COMPARISON OF THE TWO PATHWAYS 311 8.3
PHENYLACETYLENE MACROCYCLES 312 8.3.1 ORTHO PAMS 312 CONTENTS XI 8.3.2
METO-PAMS 323 8.3.3 PARA-PAMS 334 8.3.4 MIXED PAMS 335 8.4
PHENYLDIACETYLENE MACROCYCLES 338 8.4.1 ORTHO-PDUS 339 8.4.2 METO-PDMS
356 8.4.3 PARA-PDMS 361 8.4.4 MIXED PDMS 362 8.5 PHENYLTRIACETYLENE
MACROCYCLES 373 8.6 PHENYLTETRAACETYLENE MACROCYCLES 374 8.7
PHENYLOLIGOACETYLENE MACROCYCLES 377 8.8 CONCLUSIONS 378 8.9
EXPERIMENTAL 378 8.9.1 PREPARATION OF 8 FROM [(T-BUO) 3 WCT-BU)]
CATALYSIS OF 13 378 / 8.9.2 SYNTHESIS OF 8 AND 10 FROM COPPER
(2-IODOPHENYL)ACETYLIDE 379 8.9.3 PREPARATION OF 31 BY PD-CATALYZED
CYCLIZATION OF 29 379 8.9.4 PREPARATION OF 122 BY PD-MEDIATED
CYCLIZATION OF 136 37 9 8.9.5 SYNTHESIS OF 148 FROM 149 AND MO(CO) S 380
8.9.6 PREPARATION OF 189 AND 190 FROM 1,2-DIIODOTETRAFLUOROBENZENE UNDER
HAY CONDITIONS 380 8.9.7 PREPARATION OF 1 BY DEPROTECTION AND
CYCLIZATION OF 223 380 8.9.8 SYNTHESIS OF 304 BY PHOTOLYSIS OF DEWAR
BENZENE 305 381 8.9.9 PREPARATION OF 332 AND 333 BY
DEPROTECTION/CYCLIZATION OF 335 IN SITU 381 ACKNOWLEDGMENTS 381 9
CARBON-RICH COMPOUNDS: ACETYLENE-BASED CARBON AETIOTROPES 387 9.1
INTRODUCTION 387 9.2 LINEAR CARBON CLUSTERS 388 9.3 CARBYNE 394 9.4
LINEAR POLYYNES 397 9.5 MONOCYCLIC CARBON CLUSTERS: CYCLO[N]CARBONS 410
9.6 THREE-DIMENSIONAL MULTICYCLIC POLYYNES 415 9.7 CONCLUSION 420
ACKNOWLEDGEMENTS 420 10 SHAPE-PERSISTENT ACETYLENIC MACROCYCLES FOR
ORDERED SYSTEMS 427 10.1 INTRODUCTION 427 10.2 ORDERED SYSTEMS 429
10.2.1 HOST-GUEST COMPLEXES 429 10.2.2 TUBULAER SUPERSTRUCTURES IN
SOLUTION 433 10.2.3 THERMOTROPIC LIQUID CRYSTALS 438 10.2.4
TWO-DIMENSIONAL ORGANIZATION 442 10.3 CONCLUSIONS 446 10.4 EXPERIMENTAL
PROCEDURES 447 10.4.1 DEPROTECTION OF A CPDMS-PROTECTED ACETYLENE 447
XII CONTENTS 10.4.2 TEMPLATE-BASED OXIDATIVE CYCLODIMERIZATION OF A
RIGID BISACETYLENE 447 10.4.3 DEPROTECTION OF A MACROCYCLIC
THP-PROTECTED TETRAPHENOL 448 10.4.4 ALKYLATION OF A MACROCYCLIC
TETRAPHENOL 448 10.4.5 HYDROLYSIS OF A MACROCYCLE WITH TWO INTRAANNULAR
ESTER GROUPS 448 10.4.6 FORMATION OF A MACROCYCLE WITH TWO INTRAANNULAR
THIOETHER GROUPS 449 ACKNOWLEDGEMENTS 449 11 CHIRAL ACETYLENIC
MACROMOLECULES 453 11.1 INTRODUCTION 453 11.2 CHIRAL ACETYLENIC
DENDRIMERS 454 11.3 CHIRAL ACETYLENIC POLYMERS 460 11.3.1 CHIRAL
POLYMERS CONTAINING MAIN-CHAIN PARA-PHENYLENEETHYNYLENES 460 11.3.2
CHIRAL POLYMERS CONTAINING MAIN-CHAIN ORTJTO-PHENYLENEETHYNYLENES 468
11.3.3 CHIRAL POLYMERS CONTAINING MAIN-CHAIN RAETA-PHENYLENEETHYNYLENES
482 11.3.4 CHIRAL POLYMERS CONTAINING MAIN-CHAIN THIENYLENE-ETHYNYLENES
483 11.3.5 CHIRAL POLYMERS CONTAINING SIDE-CHAIN PHENYLENEETHYNYLENES
485 11.4 SUMMARY 490 ACKNOWLEDGEMENTS 493 11.5 EXPERIMENTAL PROCEDURES
491 11.5.1 PREPARATION OF THE CHIRAL DENDRIMERS - A TYPICAL PROCEDURE
491 11.5.2 PREPARATION OF THE CHIRAL POLYMER (I?)-18E 492 11.5.3
PREPARATION OF THE CHIRAL POLYMER (I?)-45 492 11.5.4 PREPARATION OF THE
HELICAL POLYMER (I?)-85 492 INDEX 495 /
|
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| dewey-sort | 3547.413 |
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| discipline | Chemie / Pharmazie Chemie |
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| id | DE-604.BV019661566 |
| illustrated | Illustrated |
| indexdate | 2024-07-09T20:02:24Z |
| institution | BVB |
| isbn | 3527307818 |
| language | English |
| oai_aleph_id | oai:aleph.bib-bvb.de:BVB01-012989945 |
| oclc_num | 57483840 |
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| owner_facet | DE-29T DE-703 DE-91G DE-BY-TUM DE-19 DE-BY-UBM DE-210 DE-1046 DE-83 DE-11 |
| physical | XX, 508 S. zahlr. graph. Darst. 25 cm |
| publishDate | 2005 |
| publishDateSearch | 2005 |
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| publisher | WILEY-VCH |
| record_format | marc |
| spelling | Acetylene chemistry chemistry, biology, and material science ed. by F. Diederich ... Weinheim WILEY-VCH 2005 XX, 508 S. zahlr. graph. Darst. 25 cm txt rdacontent n rdamedia nc rdacarrier Acetylene Alkine (DE-588)4141897-9 gnd rswk-swf Alkine (DE-588)4141897-9 s DE-604 Diederich, François 1952-2020 Sonstige (DE-588)109354419 oth GBV Datenaustausch application/pdf http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=012989945&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA Inhaltsverzeichnis |
| spellingShingle | Acetylene chemistry chemistry, biology, and material science Acetylene Alkine (DE-588)4141897-9 gnd |
| subject_GND | (DE-588)4141897-9 |
| title | Acetylene chemistry chemistry, biology, and material science |
| title_auth | Acetylene chemistry chemistry, biology, and material science |
| title_exact_search | Acetylene chemistry chemistry, biology, and material science |
| title_full | Acetylene chemistry chemistry, biology, and material science ed. by F. Diederich ... |
| title_fullStr | Acetylene chemistry chemistry, biology, and material science ed. by F. Diederich ... |
| title_full_unstemmed | Acetylene chemistry chemistry, biology, and material science ed. by F. Diederich ... |
| title_short | Acetylene chemistry |
| title_sort | acetylene chemistry chemistry biology and material science |
| title_sub | chemistry, biology, and material science |
| topic | Acetylene Alkine (DE-588)4141897-9 gnd |
| topic_facet | Acetylene Alkine |
| url | http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=012989945&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA |
| work_keys_str_mv | AT diederichfrancois acetylenechemistrychemistrybiologyandmaterialscience |