Organic azides: syntheses and applications
Gespeichert in:
| Weitere Verfasser: | |
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| Format: | Buch |
| Sprache: | English |
| Veröffentlicht: |
Chichester
Wiley
2010
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| Ausgabe: | 1. publ. |
| Schlagworte: | |
| Online-Zugang: | Inhaltsverzeichnis |
| Beschreibung: | XXVIII, 507 S. Ill., graph. Darst. |
| ISBN: | 9780470519981 0470519983 |
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Datensatz im Suchindex
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| adam_text | CONTENTS FOREWORDS: ROLF HUISGEN, VALERY FOKIN, AND BARRY SHARPLESS XIII
PREFACE XIX LIST OF CONTRIBUTORS XXI ABBREVIATIONS XXV PART 1: SYNTHESIS
AND SAFETY 1 1 LAB-SCALE SYNTHESIS OF AZIDO COMPOUNDS: SAFETY MEASURES
AND ANALYSIS 3 THOMAS KEICHER AND STEFAN LOEBBECKE 1.1 INTRODUCTION 3 1
.2 PROPERTIES THAT IMPOSE RESTRICTIONS ON LAB-SCALE HANDLING OF AZIDES 4
1.2.1 HYDRAZOIC ACID AND TTS METAL SALTS 4 1.2.2 ORGANIC AZIDES 5 1.3
LABORATORY SAFETY INSTRUCTIONS FOR THE SMALL-SCALE SYNTHESIS OF AZIDO
COMPOUNDS 5 1.4 ANALYZING SAFETY-RELATED PROPERTIES OF AZIDES 7 1.4.1
IMPACT SENSITIVITY TESTING 7 1.4.2 FRICTION SENSITIVITY TESTING 9 1.4.3
ESD TESTING 11 1.4.4 THERMOANALYTICAL MEASUREMENTS 13 1.4.5 CALORIMETRIC
AND GRAVIMETRIC STABILITY TESTS 19 1.4.6 KOENENTEST 23 REFERENCES 25 2
LARGE-SCALE PREPARATION AND USAGE OF AZIDES 29 JUERGEN HAASE 2.1
INTRODUCTION 29 2.2 PRECURSOR AZIDES, TECHNICAL PRODUCTION AND
PROPERTIES 30 2.2.1 SODIUM AZIDE (NAN 3 ) 30 2.2.2 TRIMETHYLSILYL AZIDE
(TMSA) 31 2.2.3 DIPHENYLPHOSPHORYL AZIDE (DPPA) 32 2.2.4 TRIBUTYLTIN
AZIDE (TBSNA) 34 2.2.5 AZIDOACETIC ACID ETHYL ESTER (AAE) 35 W CONTENTS
2.2.6 TETRABUTYLAMMONIUM AZIDE (TBAA) 35 2.2.7 OTHERS 37 2.3 EXAMPLES
FOR THE USE OF AZIDES ON A TECHNICAL SCALE 37 2.3.1 ADDITION OF NAN 3 TO
MULTIPLE CC- OR CN-BONDS 37 2.3.2 ADDITION OF ALK-N 3 AND AR-N 3 TO
MULTIPLE CC- AND/OR CN-BONDS 43 2.3.3 CARBOXYLIC ACID AZIDES: PRECURSORS
FOR ISOCYANATES 43 2.3.4 ORGANIC AZIDES: RING OPENING REACTION ON
OXIRANES AND AZIRIDINES: PACLITAXEL, TAMIFLU 43 2.3.5 ORGANIC AZIDES:
PROTECTIVE GROUP, MASKED AMINES 45 2.3.6 ORGANIC AZIDES: CROSS-LINKING
AGENTS FOR POLYMERS 47 2.4 THE FUTURE OF COMMERCIAL-SCALE AZIDE
CHEMISTRY 47 REFERENCES 48 3 SYNTHESIS OF AZIDES 53 TERESA M. V.D. PINHO
E MELO 3.1 INTRODUCTION 53 3.2 SYNTHESIS OF ALKYL AZIDES 53 3.2.1
CLASSIC NUCLEOPHILIC SUBSTITUTIONS: AZIDES FROM HALIDES, SULFONATES,
SULFITES, CARBONATES, THIOCARBONATES AND SULFONIUM SALTS 53 3.2.2 AZIDES
BY RING OPENING OF EPOXIDES AND AZIRIDINES 64 3.2.3 AZIDES BY THE
MITSUNOBU REACTION 70 3.2.4 ALKYL AZIDES FROM AMINES 71 3.2.5 ALKYL
AZIDES FROM CARBON NUCLEOPHILES AND ELECTRON-POOR SULFONYL AZIDES 75 3.3
SYNTHESIS OF ARYL AZIDES 76 3.3.1 NUCLEOPHILIC AROMATIC SUBSTITUTION: S
N AR REACTIONS 76 3.3.2 ARYL AZIDES FROM DIAZONIUM COMPOUNDS SO 3.3.3
ARYL AZIDES FROM ORGANOMETALLIC REAGENTS 80 3.3.4 ARYL AZIDES BY DIAZO
TRANSFER 83 3.3.5 ARYL AZIDES FROM HYDRAZINES AND FROM NITROSOARENES 84
3.4 SYNTHESIS OF ACYL AZIDES 84 3.4.1 ACYL AZIDES FROM MIXED ACID
CHLORIDES 84 3.4.2 ACYL AZIDES FROM MIXED ANHYDRIDES 85 3.4.3 ACYL
AZIDES BY DIRECT CONVERSION OF CARBOXYLIC ACIDS 86 3.4.4 ACYL AZIDES BY
DIRECT CONVERSION OF ALDEHYDES 88 3.4.5 ACYL AZIDES BY DIRECT CONVERSION
OF ACYLHYDRAZINES 89 3.4.6 ACYL AZIDES FROM N-ACYLBENZOTRIAZOLES 89
REFERENCES 90 4 AZIDES BY OLEFIN HYDROAZIDATION REACTIONS 95 JE ROEME
WASER AND ERICK M. CARREIRA 4.1 INTRODUCTION 95 4.2 CONJUGATE ADDITION
OF HYDRAZOIC ACID AND ITS DERIVATIVES 96 CONTENTS VII 4.3 ADDITION OF
HYDRAZOIC ACID AND ITS DERIVATIVES TO NON-ACTIVATED OLEFINS 98 4.4
COBALT-CATALYZED HYDROAZIDATION 99 4.4.1 OPTIMIZATION OF THE
COBALT-CATALYZED HYDROAZIDATION REACTION 99 4.4.2 SCOPE OF THE
HYDROAZIDATION OF OLEFINS 101 4.4.3 FURTHER PROCESS OPTIMIZATION 102
4.4.4 ONE-POT FUNCTIONALIZATION OF THE AZIDE PRODUCTS 106 4.4.5
MECHANISTIC INVESTIGATIONS 108 4.5 CONCLUSION 109 REFERENCES 109 PART 2:
REACTIONS 113 5 THE CHEMISTRY OF VINYL, ALLENYL, AND ETHYNYL AZIDES 115
KLAUS BANERT 5.1 INTRODUCTION AND EARLY SYNTHETIC METHODS FOR VINYL
AZIDES 115 5.2 ROUTES TO VINYL AZIDES DEVELOPED IN THE PERIOD 1965-70
119 5.3 NEW METHODS TO PREPARE VINYL AZIDES 126 5.4 REACTIONS OF VINYL
AZIDES 133 5.5 THE CHEMISTRY OF ALLENYL AZIDES 147 5.6 GENERATION OF
ETHYNYL AZIDES 154 5.7 CONCLUSION 156 ACKNOWLEDGMENT 157 REFERENCES 157
6 SMALL RINGS BY AZIDE CHEMISTRY 167 THOMAS L. GILCHRIST AND MARIA JOSE
ALVES 6.1 INTRODUCTION 167 6.2 2//-AZIRINES 167 6.3 AZIRIDINES 171 6.3.1
AZIRIDINES VIA NITRENE INTERMEDIATES 172 6.3.2 AZIRIDINES VIA
TRIAZOLINES 176 6.3.3 AZIRIDINES FROM EPOXIDES OR 1,2-DIOLS 181 6.3.4
AZIRIDINES FROM VINYL AZIDES VIA 2//-AZIRINES 183 6.4 TRIAZIRIDINES 185
6.5 AZETIDINONES 186 REFERENCES 187 7 SCHMIDT REARRANGEMENT REACTIONS
WITH ALKYL AZIDES 191 SCOTT GRECTAN AND JEFFREY AUBE 7.1 INTRODUCTION
AND EARLY ATTEMPTS (1940-60) 191 7.2 SCHMIDT REACTIONS OF ALKYL AZIDES
WITH CARBONYL COMPOUNDS 193 7.2.1 INTRAMOLECULAR REACTIONS 193 7.2.2
INTERMOLECULAR REACTIONS 197 7.2.3 REACTIONS OF HYDROXYALKYL AZIDES 200
W/7 CONTENTS 7.3 SCHMIDT REACTIONS OF ALKYL AZIDES WITH CARBOCATIONS 207
7.4 METAL-MEDIATED SCHMIDT REACTIONS OF ALKYL AZIDES WITH ALKENES AND
ALKYNES 211 7.5 REACTIONS OF ALKYL AZIDES WITH A,SS-UNSATURATED KETONES
214 7.6 REACTIONS OF ALKYL AZIDES WITH EPOXIDES 216 7.7 COMBINED SCHMIDT
REARRANGEMENT CASCADE REACTIONS 218 7.8 SCHMIDT REARRANGEMENTS IN THE
TOTAL SYNTHESIS OF NATURAL PRODUCTS 221 7.9 SCHMIDT REARRANGEMENTS OF
ALKYL AZIDES IN THE SYNTHESIS OF INTERESTING NON-NATURAL PRODUCTS 229
7.10 SCHMIDT REARRANGEMENTS OF HYDROXYALKYL AZIDES TOWARD BIOLOGICALLY
RELEVANT COMPOUNDS 232 7.11 FINAL COMMENTS 234 ACKNOWLEDGMENTS 235
REFERENCES 235 8 RADICAL CHEMISTRY WITH AZIDES 239 CIRIL JIMENO AND
PHILIPPE RENAUD 8.1 INTRODUCTION 239 8.2 ADDITION OF THE AZIDYL RADICAL
ONTO ALKENES 241 8.2.1 METAL GENERATED AZIDYL RADICALS 241 8.2.2
AZIDATION USING HYPERVALENT LODINE COMPOUNDS 243 8.2.3 HALOGEN AZIDES AS
A SOURCE OF AZIDYL RADICALS 244 8.2.4 ELECTROCHEMICALLY GENERATED AZIDYL
RADICALS 246 8.3 AZIDATION OF CARBON CENTERED RADICALS 246 8.3.1 RADICAL
AZIDATION 247 8.3.2 RADICAL ADDITIONS TO ALKYL AND ARYL AZIDES 255 8.4
AMINYL AND AMIDYL RADICALS VIA REDUCTION OF AZIDES 255 8.4.1 PHOTO- AND
ELECTROCHEMICAL REDUCTIONS OF ORGANIC AZIDES TO AMINES 257 8.4.2
REDUCTION OF ORGANIC AZIDES WITH METALS 257 8.4.3 REDUCTION OF ORGANIC
AZIDES WITH SML 2 258 8.4.4 RADICAL REACTIONS OF ORGANIC AZIDES WITH
TRIBUTYLTIN HYDRIDE 259 8.4.5 RADICAL REDUCTIONS OF ORGANIC AZIDES WITH
SILANES 260 8.4.6 RADICAL REACTIONS OF ORGANIC AZIDES WITH FECL 2 261
8.5 FRAGMENTATION REACTION OF OT-AZIDOALKYL RADICALS 262 8.6 CONCLUSIONS
264 REFERENCES 264 9 CYCLOADDITION REACTIONS WITH AZIDES: AN OVERVIEW
269 CHRISTINE SCHILLING, NICOLE JUNG AND STEFAN BRAESE 9.1 HUISGEN
1,3-DIPOLAR CYCLOADDITION 269 9.2 COPPER-CATALYZED AZIDE-ALKYNE
CYCLOADDITION (CUAAC) 270 9.2.1 GENERAL ASPECTS OF THE CUAAC REACTION
270 9.2.2 MECHANISM OF THE CUAAC REACTION 271 CONTENTS IX 9.3
ACCELERATION OF THE CLICK REACTION 272 9.3.1 ADDITION OF LIGANDS 272
9.3.2 ADDITION OF BASE 273 9.4 COPPER-FREE CLICK CHEMISTRY 274 9.5
RUTHENIUM-CATALYZED AZIDE-ALKYNE CYCLOADDITION (RUAAC) 275 9.6 USE OF
OTHER METALS FOR THE CYCLOADDITION OF AZIDES AND ALKYNES: NI(II),
PT(II), PD(II) 277 9.7 CYCLOADDITION REACTIONS WITH AZIDES FOR THE
SYNTHESIS OF TETRAZOLES 278 9.7.1 INTERMOLECULAR APPROACHES 278 9.7.2
INTERMOLECULAR APPROACHES 280 9.8 CLICK CHEMISTRY FOR THE SYNTHESIS OF
DIHYDROTRIAZOLES 280 9.9 CYCLOADDITION REACTIONS WITH AZIDES TO GIVE
THIATRIAZOLES 282 REFERENCES 282 10 DIPOLAR CYCLOADDITION REACTIONS IN
PEPTIDE CHEMISTRY 285 CHRISTIAN WENZEL TORN0E AND MOTTEN MELDAL 10.1
INTRODUCTION 285 10.2 AMINO ACID DERIVATIVES BY DCR 286 10.3 PEPTIDE
BACKBONE MODIFICATIONS BY DCR 288 10.4 OTHER PEPTIDE MODIFICATIONS BY
DCR 292 10.5 MACROCYCLIZATION BY DCR 302 10.6 DENDRIMERS AND POLYMERS
305 10.7 ISOTOPIC LABELING BY DCR 307 10.8 PERSPECTIVE 308 REFERENCES
309 11 PHOTOCHEMISTRY OF AZIDES: THE AZIDE/NITRENE INTERFACE 311 NINA
GRITSAN AND MATTHEW PLATZ 11.1 INTRODUCTION 311 11.2 PHOTOCHEMISTRY OF
HYDRAZOIC ACID (HN 3 ) 312 11.3 PHOTOCHEMISTRY OF ALKYL AZIDES 315 11.4
PHOTOCHEMISTRY OF VINYL AZIDES 319 11.5 PHOTOCHEMISTRY OF CARBONYL
AZIDES AND AZIDE ESTERS 321 11.5.1 PHOTOCHEMISTRY OF AZIDE ESTERS 325
11.6 PHOTOCHEMISTRY OF PHENYL AZIDE AND ITS SIMPLE DERIVATIVES 327
11.6.1 PHOTOCHEMISTRY OF PHENYL AZIDE 327 11.6.2 PHOTOCHEMISTRY OF
SIMPLE DERIVATIVES OF PHENYL AZIDE 336 11.6.3 PHOTOCHEMISTRY OF
POLYNUCLEAR AROMATIC AZIDES 355 11.7 CONCLUSION 363 ACKNOWLEDGMENTS 364
REFERENCES 364 12 ORGANOAZIDES AND TRANSITION METALS 373 WERNER R. THIEL
12.1 INTRODUCTION 373 12.2 METAL COMPLEXES CO-CRYSTALLIZED WITH AN
ORGANOAZIDE 376 X CONTENTS 12.3 CATIONIC METAL COMPLEXES WITH
ORGANOAZIDE CONTAINING ANIONS 376 12.4 METAL COMPLEXES WITH LIGANDS
BCARING A NON-COORDINATING ORGANOAZIDE UNIT 377 12.5 METAL COMPLEXES
WITH AN INTACT, COORDINATING AND LINEAR ORGANOAZIDE LIGAND 383 12.6
METAL COMPLEXES WITH AN INTACT, COORDINATING BUT BENT ORGANOAZIDE LIGAND
384 12.7 ORGANOAZIDES REACTING WITH OTHER METAL BOUND LIGANDS 385
REFERENCES 387 PART 3: MATERIAL SCIENCES 389 13 AZIDE-CONTAINING HIGH
ENERGY MATERIALS 391 THOMAS M. KLAPOETKE AND BURKHARD KRUMM 13.1
INTRODUCTION 391 13.2 ORGANIC AZIDES 391 13.2.1 ALKYL AND ALKENYL
SUBSTITUTED AZIDES 392 13.2.2 ARYL SUBSTITUTED AZIDES 400 13.2.3
HETEROCYCLES CONTAINING AZIDE GROUPS 405 ACKNOWLEDGMENTS 409 REFERENCES
409 14 AZIDE CHEMISTRY IN ROTAXANE AND CATENANE SYNTHESIS 413 STEPHANIE
DUROT, JULIEN FREY, JEAN-PIERRE SAUVAGE AND CHRISTIAN TOCK 14.1
INTRODUCTION 413 14.2 PURELY ORGANIC ROTAXANES AND CATENANES 415 14.2.1
WITH CUCURBITURILS (CB) AND CYCLODEXTRINS (CD) AS CYCLIC COMPONENTS 415
14.2.2 BASED ON HYDROGEN BONDING OR ON ORGANIC DONOR-ACCEPTOR COMPLEXES
417 14.3 TRANSITION METAL TEMPLATED APPROACHES 424 14.3.1 CU(I)
ASSEMBLED ROTAXANES 424 14.3.2 CU(I) AS BOTH A TEMPLATE AND A CATALYST
428 14.4 CONCLUSION 432 REFERENCES 433 PART 4: APPLICATION IN BIOORGANIC
CHEMISTRY 437 15 AZA-WITTIG REACTION IN NATURAL PRODUCT SYNTHESES 439
FRANCISCO PALACIOS, CONCEPCIOEN ALONSO, DOMITILA APARICIO, GLORIA
RUBIALES AND JESUS M. DE LOS SANTOS 15.1 INTRODUCTION 439 15.2
INTERMOLECULAR AZA-WITTIG REACTION 440 15.2.1 REACTION WITH CARBONYL
COMPOUNDS 440 15.2.2 REACTION WITH HETEROCUMULENE DERIVATIVES 446
CONTENTS XI 15.3 INTRAMOLECULAR AZA-WITTIG REACTION 451 15.3.1
FUNCTIONALIZED PHOSPHAZENES CONTAINING AN ALDEHYDE GROUP 451 15.3.2
FUNCTIONALIZED PHOSPHAZENES CONTAINING A KETONE GROUP 454 15.3.3
FUNCTIONALIZED PHOSPHAZENES CONTAINING AN ESTER GROUP 459 15.3.4
FUNCTIONALIZED PHOSPHAZENES CONTAINING AN AMIDE GROUP 461 15.4
CONCLUSIONS 464 ACKNOWLEDGMCNTS 465 REFERENCES 466 16 AZIDES IN
CARBOHYDRATE CHEMISTRY 469 HENNING S.G. BECKMANN AND VALENTIN WITTMANN
16.1 INTRODUCTION 469 16.2 SYNTHESIS OF AZIDE-CONTAINING CARBOHYDRATES
470 16.3 AZIDES AS PROTECTING GROUPS DURING AMINOGLYCOSIDE SYNTHESIS 472
16.4 AZIDES AS NON-PARTICIPATING NEIGHBORING GROUPS IN GLYCOSYLATIONS
474 16.5 GLYCOSYL AZIDES AS PRECURSORS FOR GLYCOSYL AMIDES 475 16.6
SYNTHESIS OF GLYCOCONJUGATES VIA AZIDE-ALKYNE [3+2] CYCLOADDITION 478
16.7 METABOLIE OLIGOSACCHARIDC ENGINEERING 483 REFERENCES 486 INDEX 491
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| spelling | Organic azides syntheses and applications eds. Stefan Bräse ... 1. publ. Chichester Wiley 2010 XXVIII, 507 S. Ill., graph. Darst. txt rdacontent n rdamedia nc rdacarrier Azides Azide (DE-588)4143789-5 gnd rswk-swf Stickstofforganische Verbindungen (DE-588)4043811-9 gnd rswk-swf Stickstofforganische Verbindungen (DE-588)4043811-9 s Azide (DE-588)4143789-5 s DE-604 Bräse, Stefan 1967- (DE-588)136312896 edt OEBV Datenaustausch application/pdf http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=019003571&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA Inhaltsverzeichnis |
| spellingShingle | Organic azides syntheses and applications Azides Azide (DE-588)4143789-5 gnd Stickstofforganische Verbindungen (DE-588)4043811-9 gnd |
| subject_GND | (DE-588)4143789-5 (DE-588)4043811-9 |
| title | Organic azides syntheses and applications |
| title_auth | Organic azides syntheses and applications |
| title_exact_search | Organic azides syntheses and applications |
| title_full | Organic azides syntheses and applications eds. Stefan Bräse ... |
| title_fullStr | Organic azides syntheses and applications eds. Stefan Bräse ... |
| title_full_unstemmed | Organic azides syntheses and applications eds. Stefan Bräse ... |
| title_short | Organic azides |
| title_sort | organic azides syntheses and applications |
| title_sub | syntheses and applications |
| topic | Azides Azide (DE-588)4143789-5 gnd Stickstofforganische Verbindungen (DE-588)4043811-9 gnd |
| topic_facet | Azides Azide Stickstofforganische Verbindungen |
| url | http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=019003571&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA |
| work_keys_str_mv | AT brasestefan organicazidessynthesesandapplications |