Modern oxidation methods:
Saved in:
| Other Authors: | |
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| Format: | Book |
| Language: | English |
| Published: |
Weinheim
Wiley-VCH-Verl.
2011
|
| Edition: | 2., completely rev. and enl. ed. |
| Subjects: | |
| Links: | http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=021152840&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA |
| Item Description: | Literaturangaben |
| Physical Description: | XV, 465 S. graph. Darst. |
| ISBN: | 9783527323203 |
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| 245 | 1 | 0 | |a Modern oxidation methods |c ed. by Jan-Erling Bäckvall |
| 250 | |a 2., completely rev. and enl. ed. | ||
| 264 | 1 | |a Weinheim |b Wiley-VCH-Verl. |c 2011 | |
| 300 | |a XV, 465 S. |b graph. Darst. | ||
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Record in the Search Index
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|---|---|
| adam_text | IMAGE 1
CONTENTS
PREFACE XI LIST OF CONTRIBUTORS XIII
1 RECENT DEVELOPMENTS IN METAL-CATALYZED DIHYDROXYLATION OF ALKENES 1
MAN KIN TSE, KRISTIN SCHROEDER, AND MATTHIAS BELTER 1.1 INTRODUCTION 1
1.2 ENVIRONMENTALLY FRIENDLY TERMINAL OXIDANTS 3 1.2.1 HYDROGEN PEROXIDE
3 1.2.2 HYPOCHLORITE 5
1.2.3 CHLORITE 8
1.2.4 OXYGEN OR AIR 9
1.3 SUPPORTED OSMIUM CATALYST 16 1.3.1 NITROGEN-GROUP DONATING SUPPORT
16 1.3.2 MICROENCAPSULATED OSO 4 17 1.3.3 SUPPORTS BEARING ALKENES 19
1.3.4 IMMOBILIZATION BY IONIC INTERACTION 21 1.4 IONIC LIQUID 22
1.5 RUTHENIUM CATALYSTS 23
1.6 IRON CATALYSTS 26
1.7 CONCLUSIONS 32
REFERENCES 32
2 TRANSITION METAL-CATALYZED EPOXIDATION OF ALKENES 37 HANS ADOLFISON
2.1 INTRODUCTION 37
2.2 CHOICE OF OXIDANT FOR SELECTIVE EPOXIDATION 38 2.3 EPOXIDATIONS OF
ALKENES CATALYZED BY EARLY TRANSITION METALS 39 2.4 MOLYBDENUM AND
TUNGSTEN-CATALYZED EPOXIDATIONS 42 2.4.1 HOMOGENEOUS CATALYSTS -
HYDROGEN PEROXIDE AS THE TERMINAL
OXIDANT 42
2.4.2 HETEROGENEOUS CATALYSTS 46 2.5 MANGANESE-CATALYZED EPOXIDATIONS 47
MODEM OXIDATION METHODS. EDITED BY JAN-ERLING BAECKVALL COPYRIGHT 2010
WILEY-VCH VERLAG GMBH & CO. KCAA, WEINHEIM ISBN: 978-3-527-32320-3
BIBLIOGRAFISCHE INFORMATIONEN HTTP://D-NB.INFO/1008558249
DIGITALISIERT DURCH
IMAGE 2
VI CONTENTS
2.6 RHENIUM-CATALYZED EPOXIDATIONS 52
2.6.1 MTO AS EPOXIDATION CATALYST - ORIGINAL FINDINGS 54 2.6.2 THE
INFLUENCE OF HETEROCYCLIC ADDITIVES 55 2.6.3 THE ROLE OF THE ADDITIVE 58
2.6.4 OTHER OXIDANTS 59
2.6.5 SOLVENTS/MEDIA 61
2.6.6 SOLID SUPPORT 63
2.6.7 ASYMMETRIC EPOXIDATIONS USING MTO 64 2.7 IRON-CATALYZED
EPOXIDATIONS 64 2.7.1 IRON-CATALYZED ASYMMETRIC EPOXIDATIONS 72 2.8
RUTHENIUM-CATALYZED EPOXIDATIONS 74 2.9 EPOXIDATIONS USING LATE
TRANSITION METALS 76 2.10 CONCLUDING REMARKS 79
REFERENCES 80
3 ORGANOCATALYTIC OXIDATION. KETONE-CATALYZED ASYMMETRIC EPOXIDATION OF
ALKENES AND SYNTHETIC APPLICATIONS 85 YIAN SHI 3.1 INTRODUCTION 85
3.2 CATALYST DEVELOPMENT 86
3.3 SYNTHETIC APPLICATIONS 98
3.4 CONCLUSION 109
REFERENCES 109
4 CATALYTIC OXIDATIONS WITH HYDROGEN PEROXIDE IN FLUORINATED ALCOHOL
SOLVENTS 117 ALBRECHT BERKESSEL
4.1 INTRODUCTION 117
4.2 PROPERTIES OF FLUORINATED ALCOHOLS 118 4.2.1 A DETAILED LOOK AT THE
HYDROGEN BOND DONOR FEATURES OF HFIP 120 4.3 EPOXIDATION OF ALKENES IN
FLUORINATED ALCOHOL SOLVENTS 123 4.3.1 ALKENE EPOXIDATION WITH HYDROGEN
PEROXIDE - IN THE ABSENCE
OF FURTHER CATALYSTS 123 4.3.1.1 ON THE MECHANISM OF EPOXIDATION
CATALYSIS BY FLUORINATED ALCOHOLS 123 4.3.2 ALKENE EPOXIDATION WITH
HYDROGEN PEROXIDE - IN THE PRESENCE
OF FURTHER CATALYSTS 129 4.3.2.1 ARSINES AND ARSINE OXIDES AS CATALYSTS
129 4.3.2.2 ARSONIC ACIDS AS CATALYSTS 130 4.3.2.3 DISELENIDES/SELENINIC
ACIDS AS CATALYSTS 132 4.3.2.4 RHENIUM COMPOUNDS AS CATALYSTS 133
4.3.2.5 FLUOROKETONES AS CATALYSTS 135 4.4 SULFOXIDATION OF THIOETHERS
IN FLUORINATED ALCOHOL SOLVENTS 136 4.5 BAEYER-VILLIGER OXIDATION OF
KETONES IN FLUORINATED
ALCOHOL SOLVENTS 136
IMAGE 3
CONTENTS VII
4.5.1 ACID-CATALYZED BAEYER-VILLIGER OXIDATION OF KETONES IN FLUORINATED
ALCOHOL SOLVENTS - MECHANISM 139 4.5.2 BAEYER-VILLIGER OXIDATION OF
KETONES IN FLUORINATED ALCOHOL SOLVENTS - CATALYSIS BY ARSONIC AND
SELENINIC ACIDS 141 4.6 EPILOG 142
REFERENCES 143
5 MODERN OXIDATION OF ALCOHOLS USING ENVIRONMENTALLY BENIGN OXIDANTS 147
ISABEL W.C.E. ARENAS AND ROGER A. SHELDON 5.1 INTRODUCTION 147
5.2 OXOAMMONIUM BASED OXIDATION OF ALCOHOLS - TEMPO AS CATALYST 147 5.3
METAL-MEDIATED OXIDATION OF ALCOHOLS-MECHANISM 151 5.4
RUTHENIUM-CATALYZED OXIDATIONS WITH O 2 153 5.5 PALLADIUM-CATALYZED
OXIDATIONS WITH O 2 163 5.5.1 GOLD NANOPARTICLES AS CATALYSTS 169 5.6
COPPER-CATALYZED OXIDATIONS WITH O 2 170 5.7 OTHER METALS AS CATALYSTS
FOR OXIDATION WITH O 2 174 5.8 CATALYTIC OXIDATION OF ALCOHOLS WITH
HYDROGEN PEROXIDE 176 5.8.1 BIOCATALYTIC OXIDATION OF ALCOHOLS 179 5.9
CONCLUDING REMARKS 180
REFERENCES 180
6 AEROBIC OXIDATIONS AND RELATED REACTIONS CATALYZED BY
JV-HYDROXYPHTHALIMIDE 187 YASUTAKA ISHII, SATOSHI SAKAGUCHI, AND YASUSHI
OBORA 6.1 INTRODUCTION 187
6.2 NHPI-CATALYZED AEROBIC OXIDATION 188 6.2.1 ALKANE OXIDATIONS WITH
DIOXYGEN 188 6.2.2 OXIDATION OF ALKYLARENES 193 6.2.2.1 SYNTHESIS OF
TEREPHTHALIC ACID 196
6.2.2.2 OXIDATION OF METHYLPYRIDINES AND METHYLQUINOLINES 199 6.2.2.3
OXIDATION OF HYDROAROMATIC AND BENZYLIC COMPOUNDS 201 6.2.3 PREPARATION
OF ACETYLENIC KETONES BY DIRECT OXIDATION OF ALKYNES 203 6.2.4 OXIDATION
OF ALCOHOLS 205 6.2.5 EPOXIDATION OF ALKENES USING DIOXYGEN AS TERMINAL
OXIDANT 208 6.2.6 BAEYER-VILLIGER OXIDATION OF KA OIL 209 6.2.7
PREPARATION OF E-CAPROLACTAM PRECURSOR FROM KA OIL 210 6.3
FUNCTIONALIZATION OF ALKANES CATALYZED BY NHPI 211 6.3.1 CARBOXYLATION
OF ALKANES WITH CO AND O 2 211 6.3.2 FIRST CATALYTIC NITRATION OF
ALKANES USING NO 2 212 6.3.3 SULFOXIDATION OF ALKANES CATALYZED BY
VANADIUM 214 6.3.4 REACTION OF NO WITH ORGANIC COMPOUNDS 217 6.3.5
NITROSATIONOFCYDOALKANESWITHT-BUONO 219 6.3.6 RITTER-TYPE REACTION WITH
CERIUM AMMONIUM NITRATE (CAN) 220
IMAGE 4
VIII CONTENTS
6.4 CARBON-CARBON BOND-FORMING REACTION VIA CATALYTIC CARBON
RADICALS GENERATION ASSISTED BY NHPI 222 6.4.1 OXYALKYLATION OF ALKENES
WITH ALKANES AND DIOXYGEN 222 6.4.2 SYNTHESIS OF A-HYDROXY-Y-LACTONES BY
ADDITION OF CC-HYDROXY CARBON RADICALS TO UNSATURATED ESTERS 223 6.4.3
HYDROXYACYLATION OF ALKENES USING 1,3-DIOXOLANES A N D DIOXYGEN 224
6.4.4 HYDROACYLATION OF ALKENES USING NHPI AS A POLARITY REVERSAL
CATALYST 226
6.4.5 CHIRAL NHPI DERIVATIVES AS ENANTIOSELECTIVE CATALYSTS: KINETIC
RESOLUTION OF OXAZOLIDINES 228 6.5 CONCLUSIONS 229
REFERENCES 230
7 RUTHENIUM-CATALYZED OXIDATION FOR ORGANIC SYNTHESIS 241 SHUN-LCHI
MURAHASHI AND NARUYOSHI KOMIYA 7.1 INTRODUCTION 241
7.2 RUO 4 -PROMOTED OXIDATION 241 7.3 OXIDATION WITH LOW-VALENT
RUTHENIUM CATALYSTS AND OXIDANTS 245 7.3.1 OXIDATION OF ALKENES 245
7.3.2 OXIDATION OF ALCOHOLS 249 7.3.3 OXIDATION OF AMINES 255
7.3.4 OXIDATION OF AMIDES AND SS-LACTAMS 260 7.3.5 OXIDATION OF PHENOLS
262 7.3.6 OXIDATION OF HYDROCARBONS 265 REFERENCES 268
8 SELECTIVE OXIDATION OF AMINES AND SULFIDES 277 JAN-E. BAECKVALL 8.1
INTRODUCTION 277
8.2 OXIDATION OF SULFIDES TO SULFOXIDES 277 8.2.1 STOICHIOMETRIC
REACTIONS 278 8.2.1.1 PERACIDS 278 8.2.1.2 DIOXIRANES 278 8.2.1.3 OXONE
AND DERIVATIVES 279 8.2.1.4 H 2 O 2 IN FLUOROUS PHASE AND RELATED
REACTIONS 279 8.2.2 CHEMOCATALYTIC REACTIONS 280 8.2.2.1 H 2 O 2 AS
TERMINAL OXIDANT 280 8.2.2.2 MOLECULAR OXYGEN AS TERMINAL OXIDANT 293
8.2.2.3 ALKYL HYDROPEROXIDES AS TERMINAL OXIDANT 295 8.2.2.4 OTHER
OXIDANTS IN CATALYTIC REACTIONS 297
8.2.3 BIOCATALYTIC REACTIONS 297 8.2.3.1 PEROXIDASES 298 8.2.3.2 KETONE
MONOOXYGENASES 299 8.3 OXIDATION OF TERTIARY AMINES TO N-OXIDES 300
8.3.1 STOICHIOMETRIC REACTIONS 300 8.3.2 CHEMOCATALYTIC OXIDATIONS 302
IMAGE 5
CONTENTS IX
8.3.3 BIOCATALYTIC OXIDATION 306
8.3.4 APPLICATIONS OF AMINE N-OXIDATION IN COUPLED CATALYTIC PROCESSES
306 8.4 CONCLUDING REMARKS 308
REFERENCES 309
9 LIQUID PHASE OXIDATION REACTIONS CATALYZED BY POLYOXOMETALATES 315
RONNY NEUMANN 9.1 INTRODUCTION 315
9.2 POLYOXOMETALATES (POMS) 316 9.3 OXIDATION WITH MONO-OXYGEN DONORS
317 9.4 OXIDATION WITH PEROXYGEN COMPOUNDS 323
9.5 OXIDATION WITH MOLECULAR OXYGEN 331 9.6 HETEROGENIZATION OF
HOMOGENEOUS REACTIONS - SOLID-LIQUID, LIQUID-LIQUID, AND ALTERNATIVE
REACTION SYSTEMS 341 9.6.1 SOLID-LIQUID REACTIONS 341 9.6.2
LIQUID-LIQUID REACTIONS AND REACTIONS IN ALTERNATIVE MEDIA 343 9.7
CONCLUSION 346
REFERENCES 346
10 OXIDATION OF CARBONYL COMPOUNDS 353 ERIC V.JOHNSTON ANDJAN-E.
BAECKVALL 10.1 INTRODUCTION 353
10.2 OXIDATION OF ALDEHYDES TO CARBOXYLIC ACIDS 353 10.2.1 METAL-FREE
OXIDATION OF ALDEHYDES TO CARBOXYLIC ACIDS 354 10.2.2 METAL-CATALYZED
OXIDATION OF ALDEHYDES TO CARBOXYLIC ACIDS 355 10.3 OXIDATION OF KETONES
356 10.3.1 BAEYER-VILLIGER REACTIONS 356 10.3.2 CATALYTIC ASYMMETRIC
BAEYER-VILLIGER REACTIONS 356 10.3.2.1 CHEMOCATALYTIC VERSIONS 357
10.3.2.2 BIOCATALYTIC VERSIONS 358
REFERENCES 365
11 MANGANESE-CATALYZED OXIDATION WITH HYDROGEN PEROXIDE 371 WESLEY R.
BROWNE, JOHANNES W. DE BOER, DIRK PIJPER, JELLE BRINKSMA, RONALD HAGE,
AND BEN L PERINGA 11.1 INTRODUCTION 371
11.2 BIO-INSPIRED MANGANESE OXIDATION CATALYSTS 372 11.3
MANGANESE-CATALYZED BLEACHING 375 11.4 EPOXIDATION AND
CIS-DIHYDROXYLATION OF ALKENES 375 11.4.1 MANGANESE SALTS 376
11.4.2 PORPHYRIN-BASED CATALYSIS 378 11.4.3 SALEN-BASED SYSTEMS 381
11.4.4 TRI-AND TETRA-AZACYDOALKANE DERIVATIVES 385 11.4.4.1
TETRA-AZACYDOALKANE DERIVATIVES 386 11.4.4.2 TRIAZACYDONONANE
DERIVATIVES 387
IMAGE 6
X| CONTENTS
11.4.4.3 MANGANESE COMPLEXES FOR ALKENE OXIDATION BASED
ON PYRIDYL IIGANDS 403 11.5 MANGANESE CATALYSTS FOR THE OXIDATION OF
ALKANES, ALCOHOLS, AND ALDEHYDES 406 11.5.1 OXIDATION OF ALKANES 406
11.5.2 OXIDATION OF ALCOHOLS AND ALDEHYDES 407 11.5.3 SULFIDES,
SULFOXIDES, AND SULFONES 408 11.6 CONCLUSIONS 412
REFERENCES 412
12 BIOOXIDATION WITH CYTOCHROME P450 MONOOXYGENASES 421 MARCO CIRHARD
AND VIADA B. URLACHER 12.1 INTRODUCTION 421
12.2 PROPERTIES OF CYTOCHROME P450 MONOOXYGENASES 422 12.2.1 STRUCTURE
422
12.2.2 ENZYMOLOGY 423 12.2.3 REACTIONS CATALYZED BY P450S 425 12.2.4
P450S AS INDUSTRIAL BIOCATALYSTS 429 12.2.4.1 ADVANTAGES 429 12.2.4.2
CHALLENGES IN THE DEVELOPMENT OF TECHNICAL P450 APPLICATIONS 429
12.2.4.3 GENERAL ASPECTS OF INDUSTRIAL APPLICATION AND ENGINEERING
OFP450S 430 12.3 APPLICATION AND ENGINEERING OF P450S FOR THE
PHARMACEUTICAL INDUSTRY 430 12.3.1 MICROBIAL OXIDATIONS WITH P450S FOR
SYNTHESIS
OF PHARMACEUTICALS 431 12.3.2 APPLICATION OF MAMMALIAN P450S FOR DRUG
DEVELOPMENT 434 12.3.2.1 ENHANCEMENT OF RECOMBINANT EXPRESSION IN E.
COLI 435 12.3.2.2 ENHANCEMENT OF ACTIVITY AND SELECTIVITY AND
ENGINEERING OF
NOVEL ACTIVITIES 436
12.3.2.3 CONSTRUCTION OF ARTIFICIAL SELF-SUFFICIENT FUSION PROTEINS 436
12.4 APPLICATION OF P450S FOR SYNTHESIS OF FINE CHEMICALS 437 12.5
ENGINEERING OF P450S FOR BIOCATALYSIS 438 12.5.1 COFACTOR SUBSTITUTION
AND REGENERATION 438 12.5.1.1 COFACTOR SUBSTITUTION IN VITRO 438
12.5.1.2 COFACTOR REGENERATION IN VITRO 439 12.5.1.3 COFACTOR
REGENERATION IN WHOLE-CELLS 439 12.5.2 CONSTRUCTION OF ARTIFICIAL FUSION
PROTEINS 440 12.5.3 ENGINEERING OF NEW SUBSTRATE SPECIFICITIES 440
12.5.3.1 P450 CAM FROM PSEUDOMONAS PUTIDA 440 12.5.3.2 P450 BM3 FROM
BACILLUS MEGATERIUM 442 12.6 FUTURE TRENDS 443
REFERENCES 444
INDEX 451
|
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| indexdate | 2024-12-20T14:47:22Z |
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| isbn | 9783527323203 |
| language | English |
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| oclc_num | 693885708 |
| open_access_boolean | |
| owner | DE-29T DE-11 DE-92 |
| owner_facet | DE-29T DE-11 DE-92 |
| physical | XV, 465 S. graph. Darst. |
| publishDate | 2011 |
| publishDateSearch | 2011 |
| publishDateSort | 2011 |
| publisher | Wiley-VCH-Verl. |
| record_format | marc |
| spellingShingle | Modern oxidation methods Oxidation (DE-588)4137187-2 gnd Organische Verbindungen (DE-588)4043816-8 gnd Methode (DE-588)4038971-6 gnd |
| subject_GND | (DE-588)4137187-2 (DE-588)4043816-8 (DE-588)4038971-6 |
| title | Modern oxidation methods |
| title_auth | Modern oxidation methods |
| title_exact_search | Modern oxidation methods |
| title_full | Modern oxidation methods ed. by Jan-Erling Bäckvall |
| title_fullStr | Modern oxidation methods ed. by Jan-Erling Bäckvall |
| title_full_unstemmed | Modern oxidation methods ed. by Jan-Erling Bäckvall |
| title_short | Modern oxidation methods |
| title_sort | modern oxidation methods |
| topic | Oxidation (DE-588)4137187-2 gnd Organische Verbindungen (DE-588)4043816-8 gnd Methode (DE-588)4038971-6 gnd |
| topic_facet | Oxidation Organische Verbindungen Methode |
| url | http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=021152840&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA |
| work_keys_str_mv | AT backvalljane modernoxidationmethods |