Modern fluoroorganic chemistry: synthesis, reactivity, applications
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| Main Author: | |
|---|---|
| Format: | Book |
| Language: | English |
| Published: |
Weinheim
Wiley-VCH
2013
|
| Edition: | 2., completely rev. and enl. ed. |
| Subjects: | |
| Online Access: | Inhaltstext Inhaltsverzeichnis |
| Physical Description: | XX, 379 S. Ill., graph. Darst. 240 mm x 170 mm |
| ISBN: | 9783527331666 3527331662 |
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| 250 | |a 2., completely rev. and enl. ed. | ||
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| 300 | |a XX, 379 S. |b Ill., graph. Darst. |c 240 mm x 170 mm | ||
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Record in the Search Index
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IMAGE 1
V I I
CONTENTS
PREFACE TO T H E SECOND EDITION X I I I PREFACE TO T H E FIRST EDITION
XV
ABBREVIATIONS X V I I
1 INTRODUCTION 1
1.1 WHY ORGANOFLUORINE CHEMISTRY? 1
1.2 HISTORY 1
1.3 THE BASIC MATERIALS 3
1.3.1 HYDROFLUORIC ACID 3
1.3.2 FLUORINE 5
1.4 T H E UNIQUE PROPERTIES O F ORGANOFLUORINE COMPOUNDS 7
1.4.1 PHYSICAL PROPERTIES 7
1.4.2 CHEMICAL PROPERTIES 1 3
1.4.3 ECOLOGICAL IMPACT 1 5
1.4.3.1 OZONE DEPLETION BY CHLOROFLUOROCARBONS 1 5
1.4.3.2 GREENHOUSE EFFECT 1 7
1.4.4 PHYSIOLOGICAL PROPERTIES 1 8
1.4.5 ANALYSIS O F FLUOROCHEMICALS: 19F NMR SPECTROSCOPY 2 0
REFERENCES 2 1
PART I SYNTHESIS O F COMPLEX ORGANOFLUORINE COMPOUNDS 2 5
2 INTRODUCTION O F FLUORINE 2 7
2.1 PERFLUORINATION A N D SELECTIVE DIRECT FLUORINATION 2 7
2.2 ELECTROCHEMICAL FLUORINATION (ECF) 3 4
2.3 NUCLEOPHILIC FLUORINATION 3 6
2.3.1 FINKELSTEIN EXCHANGE 3 6
2.3.2 "NAKED" FLUORIDE 3 6
2.3.3 LEWIS ACID-ASSISTED FLUORINATION 3 9
2.3.4 THE "GENERAL FLUORINE EFFECT" 4 1
2.3.5 A M I N E - H Y D R O G E N FLUORIDE A N D ETHER-HYDROGEN FLUORIDE
REAGENTS 4 2
HTTP://D-NB.INFO/1026137314
IMAGE 2
V I I I CONTENTS
2.3.6 HYDROFLUORINATION, HALOFLUORINATION, A N D EPOXIDE RING OPENING 43
2.4 SYNTHESIS A N D REACTIVITY O F FLUOROAROMATIC COMPOUNDS 4 6 2.4.1
SYNTHESIS O F FLUOROAROMATIC COMPOUNDS 46 2.4.2 REDUCTIVE AROMATIZATION
4 7
2.4.3 T H E BALZ-SCHIEMANN REACTION 4 7
2.4.4 T H E FLUOROFORMATE PROCESS 4 9
2.4.5 TRANSITION METAL-CATALYZED AROMATIC FLUORINATION 4 9 2.4.6 THE
HALEX PROCESS 5 5
2.4.7 THINK NEGATIVE! - "ORTHOGONAL" REACTIVITY O F PERFLUOROAROMATIC A
N D PERFLUOROOLEFINIC SYSTEMS 5 5 2.4.8 THE "SPECIAL FLUORINE EFFECT" 5
8
2.4.9 AROMATIC NUCLEOPHILIC SUBSTITUTION 59
2.4.10 ACTIVATION O F THE CARBON-FLUORINE BOND BY TRANSITION METALS 6 3
2.4.10.1 ELECTROPHILICALLY ACTIVATED ARYLATION BY FLUOROARENES 63
2.4.11 ACTIVATION O F FLUOROAROMATIC COMPOUNDS BY ORTHO-METALATION 64
2.5 TRANSFORMATIONS O F FUNCTIONAL GROUPS 6 7
2.5.1 HYDROXY INTO FLUORO 6 7
2.5.1.1 TWO-STEP ACTIVATION-FLUORINATION 68 2.5.1.2 A,
A-DIFLUOROALKYLAMINE A N D OI-FLUOROENAMINE REAGENTS 68 2.5.1.3 SULFUR
TETRAFLUORIDE, DAST, A N D RELATED REAGENTS 7 1 2.5.1.4 A M I N E - H Y
D R O G E N FLUORIDE REAGENTS 7 3
2.5.2 CONVERSION O F CARBONYL INTO GEM-DIFLUOROMETHYLENE 74
2.5.2.1 SULFUR TETRAFLUORIDE, DAST, A N D RELATED REAGENTS 74 2.5.3
CARBOXYL INTO TRIFLUOROMETHYL 77
2.5.4 OXIDATIVE FLUORODESULFURATION 78
2.6 "ELECTROPHILIC" FLUORINATION 8 5
2.6.1 XENON DIFLUORIDE 8 5
2.6.2 PERCHLORYL FLUORIDE A N D HYPOFLUORIDES 86 2.6.3 "NF"-REAGENTS 8 8
REFERENCES 98
3 PERFLUOROALKYLATION 107
3.1 RADICAL PERFLUOROALKYLATION 1 0 7
3.1.1 STRUCTURE, PROPERTIES, A N D REACTIVITY O F PERFLUOROALKYL
RADICALS 1 0 7
3.1.2 PREPARATIVELY USEFUL REACTIONS O F PERFLUOROALKYL RADICALS 1 1 0
3.1.3 "INVERSE" RADICAL ADDITION O F ALKYL RADICALS TO PERFLUOROOLEFINS
1 1 5
3.2 NUCLEOPHILIC PERFLUOROALKYLATION 1 1 8
3.2.1 PROPERTIES, STABILITY, A N D REACTIVITY O F FLUORINATED CARBANIONS
1 1 8
3.2.2 PERFLUOROALKYL METAL COMPOUNDS 1 2 0
3.2.3 PERFLUOROALKYLSILANES 1 3 0
3.3 "ELECTROPHILIC" PERFLUOROALKYLATION 1 3 9
3.3.1 PROPERTIES A N D STABILITY O F FLUORINATED CARBOCATIONS 1 3 9
3.3.2 ARYLPERFLUOROALKYLIODONIUM SALTS 1 4 2
3.3.3 PERFLUOROALKYL SULFONIUM, SELENONIUM, TELLURONIUM, A N D OXONIUM
SALTS 1 4 9
IMAGE 3
.3.4
.4
.1
. 2
.3
.4
.1
. 2
. 1
. 1
. 2
.3
.1
. 2
.3
.4 .4.1 .4.2 .4.2. .4.3 .4.3.
.4.3.: .4.3. .4.3.
CONTENTS | ( X
FLUORINATED JOHNSON REAGENTS 156
DIFLUOROCARBENE A N D FLUORINATED CYCLOPROPANES 156 REFERENCES 1 6 0
SELECTED FLUORINATED STRUCTURES AND REACTION TYPES 1 6 9
DIFLUOROMETHYLATION A N D HALODIFLUOROMETHYLATION 169
THE PERFLUOROALKOXY GROUP 1 7 2 T H E PERFLUOROALKYLTHIO GROUP A N D
SULFUR-BASED
SUPER-ELECTRON-WITHDRAWING GROUPS 176 THE PENTAFLUOROSULFANYL GROUP A N
D RELATED STRUCTURES 1 7 9 REFERENCES 1 8 8
THE CHEMISTRY O F HIGHLY FLUORINATED OLEFINS 1 9 3
FLUORINATED POLYMETHINES 1 9 3
FLUORINATED ENOL ETHERS AS SYNTHETIC BUILDING BLOCKS 1 9 8
REFERENCES 2 0 5
PART II FLUOROUS CHEMISTRY 2 0 7
FLUOROUS CHEMISTRY 2 0 9
FLUOROUS BIPHASE CATALYSIS 2 0 9
REFERENCES 2 2 4
FLUOROUS SYNTHESIS AND COMBINATORIAL CHEMISTRY 2 2 7
FLUOROUS SYNTHESIS 2 2 7
SEPARATION O N FLUOROUS STATIONARY PHASES 2 3 2
FLUOROUS CONCEPTS I N COMBINATORIAL CHEMISTRY 2 3 3
REFERENCES 2 4 2
PART III APPLICATIONS O F ORGANOFLUORINE COMPOUNDS 2 4 5
HALOFLUOROCARBONS, HYDROFLUOROCARBONS, AND RELATED
COMPOUNDS 247 POLYMERS A N D LUBRICANTS 249 APPLICATIONS I N THE
ELECTRONICS INDUSTRY 256 FLUORINATED DYES 2 5 8
LIQUID CRYSTALS FOR ACTIVE MATRIX LIQUID CRYSTAL DISPLAYS 2 6 0
CALAMITIC LIQUID CRYSTALS: A SHORT INTRODUCTION 260
FUNCTIONING O F ACTIVE MATRIX LCDS 261 THE PHYSICAL PROPERTIES O F
NEMATIC LIQUID CRYSTALS 2 6 4 W H Y FLUORINATED LIQUID CRYSTALS? 267
IMPROVED MESOPHASE BEHAVIOR BY LATERAL FLUORINATION 267 FLUORINATED
POLAR GROUPS 269 IMPROVED RELIABILITY 274 FLUORINATED BRIDGE STRUCTURES
275
IMAGE 4
X I CONTENTS
8.4.4 CONCLUSION A N D OUTLOOK 279
8.5 FLUORINE I N ORGANIC ELECTRONICS 2 8 1
8.5.1 ORGANIC FIELD EFFECT TRANSISTORS (OFETS) 2 8 1
8.5.2 ORGANIC LIGHT-EMITTING DIODES (OLEDS) 2 9 0
REFERENCES 2 9 3
9 PHARMACEUTICALS AND OTHER BIOMEDICAL APPLICATIONS 299
9.1 W H Y FLUORINATED PHARMACEUTICALS? 299
9.2 LIPOPHILICITY A N D SUBSTITUENT EFFECTS 3 0 0
9.3 HYDROGEN BONDING A N D ELECTROSTATIC INTERACTIONS 3 0 3
9.4 STEREOELECTRONIC EFFECTS A N D CONFORMATION 306
9.5 METABOLIC STABILIZATION A N D MODULATION O F REACTION CENTERS 3 1 0
9.6 BIOISOSTERIC MIMICKING 3 1 6
9.7 MECHANISM-BASED "SUICIDE" INHIBITION 3 2 5
9.8 FLUORINATED RADIOPHARMACEUTICALS 329
9.9 INHALATION ANESTHETICS 3 3 3
9.10 BLOOD SUBSTITUTES A N D RESPIRATORY FLUIDS 334
9.11 CONTRAST MEDIA A N D MEDICAL DIAGNOSTICS 335
9.12 AGRICULTURAL CHEMISTRY 336
REFERENCES 3 4 0
APPENDIX A: TYPICAL SYNTHETIC PROCEDURES 3 5 1
A . L SELECTIVE DIRECT FLUORINATION 3 5 1
A . L . L GENERAL REMARKS 3 5 1
A.L.2 FLUORINATION O F DIETHYL MALONATE (1) TO DIETHYL FLUOROMALONATE
(2) 352
A.L.3 SYNTHESIS O F BIS(4-NITROPHENYL)TETRAFLUOROSULFURANE (4) (ISOMERIC
MIXTURE: 15% TRANS- 85% CIS) 352 A. 1.4 ISOMERIZATION TO TRANS-4 353
A.2 HYDROFLUORINATION A N D HALOFLUORINATION 353
A.2.1 GENERAL REMARKS 353
A.2.2 SYNTHESIS O F T H E LIQUID CRYSTAL 6 354
A.2.3 SYNTHESIS O F 8 354
A.3 ELECTROPHILIC FLUORINATION WITH F-TEDA-BF4 (SELECTFLUOR) 355 A.3.1
SYNTHESIS O F THE FLUOROSTEROID 11 355
A.3.2 SYNTHESIS O F DIETHYL FLUOROPHENYLMALONATE (13) 355 A.4
FLUORINATIONS WITH DAST A N D BAST (DEOXOFLUOR) 356 A.4.1 GENERAL
REMARKS 356
A.4.2 GENERAL PROCEDURE FOR FLUORINATION O F ALCOHOLS 356 A.4.3 GENERAL
PROCEDURE FOR FLUORINATION O F ALDEHYDES A N D KETONES 3 5 7 A.5
FLUORINATION O F A CARBOXYLIC ACID WITH SULFUR TETRAFLUORIDE 3 5 8 A.5.1
GENERAL REMARKS 358
A.5.2 SYNTHESIS O F 4-BROMO-2-(TRIFLUOROMETHYL)THIAZOLE (23) 358 A.6
GENERATION O F A TRIFLUOROMETHOXY GROUP BY OXIDATIVE FLUORODESULFURATION
O F A XANTHOGENATE 358
IMAGE 5
CONTENTS I X I
A.6.1 SYNTHESIS O F THE LIQUID CRYSTAL 25 3 5 8
A.7 OXIDATIVE ALKOXYDIFLUORODESULFURATION O F DITHIANYLIUM SALTS 3 5 9
A . 7 . 1 DITHIANYLIUM TRIFLATE (27) 3 5 9
A.7.2 SYNTHESIS O F 28 FROM THE DITHIANYLIUM SALT 27 3 6 0
A.7.3 SYNTHESIS O F 28 FROM THE KETENEDITHIOKETAL 29 3 6 0
A.8 ELECTROPHILIC TRIFLUOROMETHYLATION WITH UMEMOTO'S REAGENTS 3 6 1
A.8.1 TRIFLUOROMETHYLATION O F THE TRIMETHYLSILYLDIENOL ETHER 30 3 6 1
A.9 NUCLEOPHILIC TRIFLUOROMETHYLATION WITH MEASICFJ 3 6 2
A.9.1 NUCLEOPHILIC TRIFLUOROMETHYLATION O F KETONE 33 3 6 2
A.10 TRANSITION METAL-MEDIATED AROMATIC PERFLUOROALKYLATION 3 6 2
A.10.1 COPPER-MEDIATED TRIFLUOROMETHYLATION O F 36 USING SILANE
REAGENTS 362
A.10.2 PALLADIUM-MEDIATED TRIFLUOROMETHYLATION O F ARYL CHLORIDE 41 3 6
3 A . L L COPPER-MEDIATED INTRODUCTION O F THE TRIFLUOROMETHYLTHIO GROUP
3 6 4
A . L L . L PREPARATION O F TRIFLUOROMETHYLTHIO COPPER REAGENT 43 3 6 4
A.11.2 REACTION O F CUSCF 3 W I T H 4-IODOANISOLE (44) 3 6 4
A.12 SUBSTITUTION REACTIONS O N FLUOROOLEFINS A N D FLUOROARENES 365
A.12.1 PREPARATION O F A, FI-DIFLUORO-P-CHLOROSTYRENES (47) 3 6 5 A . 1
2 . 2 PREPARATION O F A, FI-DIFLUOROCINNAMIC ACID (48) 3 6 5
A.12.3 ORTHO-METALATION O F 1,2-DIFLUOROBENZENE (49) WITH LDA 365
A. 13 REACTIONS WITH DIFLUOROENOLATES 3 6 6
A.13.1 PREPARATION O F THE TRIMETHYLSILYL DIFLUOROENOL ETHER 52 3 6 6
A.13.2 ADDITION O F 52 TO CARBONYL COMPOUNDS 3 6 7
REFERENCES 3 6 7
APPENDIX B: INDEX O F SYNTHETIC CONVERSIONS 369
INDEX 3 7 3 |
| any_adam_object | 1 |
| author | Kirsch, Peer 1965- |
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| building | Verbundindex |
| bvnumber | BV040798613 |
| classification_rvk | VK 7710 |
| classification_tum | CHE 631f |
| ctrlnum | (OCoLC)839924055 (DE-599)DNB1026137314 |
| dewey-full | 547.02 |
| dewey-hundreds | 500 - Natural sciences and mathematics |
| dewey-ones | 547 - Organic chemistry |
| dewey-raw | 547.02 |
| dewey-search | 547.02 |
| dewey-sort | 3547.02 |
| dewey-tens | 540 - Chemistry and allied sciences |
| discipline | Chemie / Pharmazie Chemie |
| edition | 2., completely rev. and enl. ed. |
| format | Book |
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| publisher | Wiley-VCH |
| record_format | marc |
| spelling | Kirsch, Peer 1965- Verfasser (DE-588)129277037 aut Modern fluoroorganic chemistry synthesis, reactivity, applications Peer Kirsch 2., completely rev. and enl. ed. Weinheim Wiley-VCH 2013 XX, 379 S. Ill., graph. Darst. 240 mm x 170 mm txt rdacontent n rdamedia nc rdacarrier Fluororganische Verbindungen (DE-588)4154846-2 gnd rswk-swf 1\p (DE-588)4123623-3 Lehrbuch gnd-content Fluororganische Verbindungen (DE-588)4154846-2 s DE-604 X:MVB text/html http://deposit.dnb.de/cgi-bin/dokserv?id=4126138&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=025778759&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 |
| spellingShingle | Kirsch, Peer 1965- Modern fluoroorganic chemistry synthesis, reactivity, applications Fluororganische Verbindungen (DE-588)4154846-2 gnd |
| subject_GND | (DE-588)4154846-2 (DE-588)4123623-3 |
| title | Modern fluoroorganic chemistry synthesis, reactivity, applications |
| title_auth | Modern fluoroorganic chemistry synthesis, reactivity, applications |
| title_exact_search | Modern fluoroorganic chemistry synthesis, reactivity, applications |
| title_full | Modern fluoroorganic chemistry synthesis, reactivity, applications Peer Kirsch |
| title_fullStr | Modern fluoroorganic chemistry synthesis, reactivity, applications Peer Kirsch |
| title_full_unstemmed | Modern fluoroorganic chemistry synthesis, reactivity, applications Peer Kirsch |
| title_short | Modern fluoroorganic chemistry |
| title_sort | modern fluoroorganic chemistry synthesis reactivity applications |
| title_sub | synthesis, reactivity, applications |
| topic | Fluororganische Verbindungen (DE-588)4154846-2 gnd |
| topic_facet | Fluororganische Verbindungen Lehrbuch |
| url | http://deposit.dnb.de/cgi-bin/dokserv?id=4126138&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=025778759&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA |
| work_keys_str_mv | AT kirschpeer modernfluoroorganicchemistrysynthesisreactivityapplications |