Verfügbarkeit: Organic and inorganic fluorine chemistry

Organic and inorganic fluorine chemistry: methods and applications

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Bibliographische Detailangaben
1. Verfasser:	Haupt, Axel 1974- (VerfasserIn)
Format:	Buch
Sprache:	English
Veröffentlicht:	Berlin ; Boston De Gruyter [2021]
Schriftenreihe:	De Gruyter Graduate
Schlagworte:	Anorganische Verbindungen Fluororganische Verbindungen Fluorverbindungen Fluoride TB: Textbook
Online-Zugang:	Kurzbeschreibung Inhaltsverzeichnis
Beschreibung:	XVI, 625 Seiten Illustrationen 24 cm x 17 cm
ISBN:	9783110659290 3110659298

Internformat

MARC


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Datensatz im Suchindex

_version_	1804182333831512064
adam_text	CONTENTS PREFACE * V FOREWORD * VII PART A: INTRODUCTION TO FLUORINE CHEMISTRY 1 1.1 1.2 1.3 1.4 SOURCES OF FLUORINE IN NATURE * 5 THE FLUOROSPHERE * 5 FLUORIDE SOURCES AND ELEMENTAL FLUORINE IN MINERALS * 5 NATURAL ORGANOFLUORINE COMPOUNDS * 7 STUDY QUESTIONS * 8 2 2.1 2.2 2.3 2.4 2.5 ELEMENTAL FLUORINE * 9 PROPERTIES AND GENERAL REACTIVITY * 9 POLYFLUORIDE ANIONS * 11 PREPARATION OF F 2 * 11 WORKING WITH ELEMENTAL FLUORINE AND FLUORINATED COMPOUNDS * 13 STUDY QUESTIONS * 14 3 3.1 3.2 3.3 3.4 3.5 3.6 3.7 HYDROGEN FLUORIDE * 15 PREPARATION, GENERAL PROPERTIES AND APPLICATIONS * 15 STRUCTURAL PROPERTIES * 15 ANHYDROUS AND AQUEOUS HYDROGEN FLUORIDE * 16 SALTS OF HYDROGEN FLUORIDE * 17 NAKED FLUORIDE AND LIGAND PROPERTIES * 18 ANHYDROUS HYDROGEN FLUORIDE AS REACTION MEDIUM * 19 STUDY QUESTIONS * 21 4 4.1 4.2 4.3 4.4 PREPARATION OF FLUORINATED COMPOUNDS * 23 TRANSFORMATIONS WITH GASEOUS FLUORINATING AGENTS * 23 SOLID-STATE REACTIONS AND FLUORINATIONS IN FLUX * 27 FLUORINATION IN SOLUTION PHASE * 27 STUDY QUESTIONS * 28 5 5.1 5.2 5.3 COMMON SOLID-STATE STRUCTURES OF INORGANIC FLUORIDES * 31 BINARY FLUORIDES * 31 TERNARY AND QUATERNARY FLUORIDES * 33 STUDY QUESTIONS * 33 X ---- * CONTENTS 6 PROPERTIES OF FLUORINATED COMPOUNDS * 35 7 7.1 7.2 7.3 7.4 HEALTH AND ENVIRONMENTAL ASPECTS OF FLUORINATED COMPOUNDS * 37 IMPACT OF FLUORINATED COMPOUNDS ON HUMANS AND ANIMALS ----- 37 FLUORINATED COMPOUNDS IN THE ENVIRONMENT ----- 38 PERSPECTIVES IN THE USE OF FLUORINATED COMPOUNDS * 41 STUDY QUESTIONS ----- 42 8 8.1 8.2 8.3 8.4 19 F-NMR - AN IMPORTANT ANALYTICAL TOOL FOR FLUORINE CHEMISTS * 43 GENERAL ASPECTS AND REFERENCE SUBSTANCES -----43 CHEMICAL SHIFTS -----44 COUPLING CONSTANTS ----- 47 STUDY QUESTIONS ----- 48 PART B: INORGANIC FLUORINE CHEMISTRY 9 9.1 9.1.1 9.1.2 9.2 MAIN GROUP ELEMENT FLUORIDES * 55 GROUP 1: LITHIUM, SODIUM, POTASSIUM, RUBIDIUM, CESIUM ----- 55 THE ALKALI METAL FLUORIDES ----- 55 STUDY QUESTIONS ----- 56 GROUP 2: BERYLLIUM, MAGNESIUM, CALCIUM, STRONTIUM, BARIUM, RADIUM ----- 56 9.2.1 9.2.2 9.2.3 9.3 9.3.1 9.3.2 9.3.3 9.4 9.4.1 9.4.2 9.4.3 9.5 9.5.1 9.5.2 9.5.3 9.6 9.6.1 9.6.2 9.6.3 BERYLLIUM ----- 56 MAGNESIUM, CALCIUM, STRONTIUM, BARIUM AND RADIUM ----- 58 STUDY QUESTIONS ----- 59 GROUP 13: BORON, ALUMINIUM, GALLIUM, INDIUM, THALLIUM ----- 59 BORON ----- 59 ALUMINIUM, GALLIUM, INDIUM, THALLIUM ----- 64 STUDY QUESTIONS ----- 68 GROUP 14: CARBON, SILICON, GERMANIUM, TIN, LEAD * 68 CARBON ----- 68 SILICON, GERMANIUM, TIN, LEAD * 71 STUDY QUESTIONS ----- 79 GROUP 15: NITROGEN, PHOSPHORUS, ARSENIC, ANTIMONY, BISMUTH ----- 80 NITROGEN ----- 80 PHOSPHORUS, ARSENIC, ANTIMONY, BISMUTH ----- 88 STUDY QUESTIONS ----- 98 GROUP 16: OXYGEN, SULPHUR, SELENIUM, TELLURIUM, POLONIUM ----- 98 OXYGEN ----- 98 SULPHUR, SELENIUM, TELLURIUM, POLONIUM ----- 111 STUDY QUESTIONS ----- 129 CONTENTS * XI 9.7 GROUP 17: CHLORINE, BROMINE, IODINE ----- 130 9.7.1 PREPARATION OF THE HALOGEN FLUORIDES * 130 9.7.2 STRUCTURAL PROPERTIES OF THE HALOGEN FLUORIDES * 132 9.7.3 STABILITY OF THE HALOGEN FLUORIDES * 133 9.7.4 REACTIVITY OF THE HALOGEN FLUORIDES * 133 9.7.5 FLUORINATED CATIONS DERIVED FROM THE HALOGEN FLUORIDES * 135 9.7.6 FLUOROHALOGENATE ANIONS * 137 9.7.7 HALOGEN OXYFLUORIDES * 139 9.7.8 STUDY QUESTIONS ----- 146 9.8 GROUP 18: KRYPTON, XENON, RADON * 147 9.8.1 XENON * 147 9.8.2 KRYPTON ----- 157 9.8.3 RADON * 158 9.8.4 STUDY QUESTIONS ----- 159 10 TRANSITION METAL FLUORIDES AND RARE EARTH METAL FLUORIDES * 161 10.1 GROUP 3: SCANDIUM, YTTRIUM, LANTHANUM, ACTINIUM * 161 10.1.1 COMPOUNDSAND PROPERTIES * 161 10.1.2 STUDY QUESTIONS ----- 163 10.2 THE LANTHANIDES * 163 10.2.1 COMPOUNDSAND PROPERTIES ----- 163 10.2.2 STUDY QUESTIONS ----- 167 10.3 THE ACTINIDES * 168 10.3.1 COMPOUNDS AND PROPERTIES * 168 10.3.2 STUDY QUESTIONS * 179 10.4 GROUP 4: TITANIUM, ZIRCONIUM, HAFNIUM * 179 10.4.1 TITANIUM * 179 10.4.2 ZIRCONIUM AND HAFNIUM * 185 10.4.3 STUDY QUESTIONS ----- 189 10.5 GROUP 5: VANADIUM, NIOBIUM, TANTALUM * 189 10.5.1 VANADIUM * 189 10.5.2 NIOBIUM AND TANTALUM * 197 10.5.3 STUDY QUESTIONS * 203 10.6 GROUP 6: CHROMIUM, MOLYBDENUM, TUNGSTEN * 203 10.6.1 CHROMIUM ----- 203 10.6.2 MOLYBDENUM AND TUNGSTEN * 211 10.6.3 STUDY QUESTIONS * 219 10.7 GROUP 7: MANGANESE, TECHNETIUM, RHENIUM * 220 10.7.1 MANGANESE * 220 10.7.2 TECHNETIUM AND RHENIUM * 226 10.7.3 STUDY QUESTIONS * 234 10.8 IRON, COBALT, NICKEL * 235 XII * CONTENTS 10.8.1 10.8.2 10.9 COMPOUNDS AND PROPERTIES * 235 STUDY QUESTIONS ----- 245 THE PLATINUM METALS: RUTHENIUM, OSMIUM, RHODIUM, IRIDIUM, PLATINUM, PALLADIUM ----- 245 10.9.1 10.9.2 10.10 10.10.1 10.10.2 10.10.3 10.10.4 10.11 10.11.1 10.11.2 10.11.3 10.11.4 10.11.5 COMPOUNDS AND PROPERTIES ----- 245 STUDY QUESTIONS ----- 259 GROUP 11: COPPER, SILVER, GOLD ----- 260 COPPER ----- 260 SILVER ----- 264 GOLD ----- 267 STUDY QUESTIONS -----272 GROUP 12: ZINC, CADMIUM, MERCURY ----- 272 ZINC ----- 272 CADMIUM ----- 273 MERCURY ----- 274 ZINC, CADMIUM AND MERCURY IN HIGHER OXIDATION STATES ----- 277 STUDY QUESTIONS ----- 278 PARTC: ORGANIC FLUORINE CHEMISTRY 11 FLUOROORGANIC COMPOUNDS - UNUSUAL PROPERTIES AND VERSATILE APPLICATIONS * 283 11.1 11.1.1 11.1.2 11.1.3 11.1.4 11.1.5 11.1.6 11.2 PHYSICAL PROPERTIES OF FLUOROORGANIC COMPOUNDS * 283 BOILING POINTS AND DIPOLE MOMENTS * 283 SOLVENT PROPERTIES * 284 SURFACE TENSION AND SURFACE ENERGY * 285 LIPOPHILICITY ----- 285 ACIDITY AND BASICITY * 285 STUDY QUESTIONS * 286 CHEMICAL PROPERTIES AND STABILITY OF FLUOROORGANIC COMPOUNDS AND REACTIVE INTERMEDIATES * 287 11.2.1 11.2.2 11.2.3 11.2.4 11.2.5 11.2.6 11.2.7 11.3 11.3.1 11.3.2 FLUORINE AT SP 3 -CARBONS * 287 FLUORINE AT SP 2 -AND SP-CARBONS * 288 FLUORINATED CARBOCATIONS * 289 FLUORINATED CARBANIONS * 290 FLUORINATED RADICALS * 292 FLUORINATED CARBENES * 293 STUDY QUESTIONS ----- 293 APPLICATIONS OF ORGANOFLUORINE COMPOUNDS * 294 VERSATILE USES OF HALO- AND HYDROFLUOROCARBONS * 294 FLUOROPOLYMERS ----- 294 CONTENTS * XIII 11.3.3 11.3.4 11.3.5 11.3.6 11.3.7 11.3.8 11.3.9 FLUORINATED DYES * 295 FLUORINATED LIQUID CRYSTALS * 296 ORGANIC ELECTRONICS * 296 BIOLOGICALLY ACTIVE COMPOUNDS * 297 MEDICINAL DIAGNOSTICS * 298 FURTHER MEDICAL APPLICATIONS * 298 STUDY QUESTIONS * 299 12 12.1 12.1.1 12.1.2 12.1.3 12.2 12.2.1 12.2.2 12.2.3 12.3 12.3.1 12.3.2 12.3.3 12.3.4 12.3.5 12.4 12.4.1 12.4.2 12.4.3 12.5 12.6 GENERAL REACTION TYPES AND REAGENTS FOR THE INTRODUCTION OF FLUORINE * 301 DIRECT FLUORINATION AND RADICAL REACTIONS * 301 ELEMENTAL FLUORINE AND HIGH-VALENT METAL FLUORIDES * 301 RADICAL FLUORINATION USING ELECTROPHILIC FLUORINATING REAGENTS * 302 STUDY QUESTIONS * 302 ELECTROCHEMICAL FLUORINATION * 302 PREREQUISITES * 303 MECHANISTICAL ASPECTS * 303 STUDY QUESTIONS * 304 NUCLEOPHILIC FLUORINATION ----- 304 HF AND ITS COMPLEXES ----- 304 IONIC FLUORIDES * 305 MOLECULAR FLUORIDES * 307 ENZYMATIC FLUORINATION * 312 STUDY QUESTIONS * 312 ELECTROPHILIC FLUORINATION * 312 FLUOROXY COMPOUNDS, PERCHLORYL FLUORIDE AND XENON DIFLUORIDE * 313 FLUORAZA REAGENTS * 313 STUDY QUESTIONS * 316 METAL-MEDIATED REACTIONS, INCLUDING PHOTOCATALYSIS * 316 HYDRODEFLUORINATION AND DEFLUOROFUNCTIONALIZATION * 317 13 13.1 FLUORINATION OF ALIPHATIC SUBSTRATES * 319 GENERAL TRENDS IN THE SYNTHESIS OF ALIPHATIC ORGANOFLUORINE COMPOUNDS * 319 13.1.1 13.1.2 13.1.3 13.2 13.2.1 13.2.2 13.2.3 13.2.4 THE GENERAL FLUORINE EFFECT * 319 THE SPECIAL FLUORINE EFFECT * 320 STUDY QUESTIONS ----- 320 RADICAL REACTIONS AND DIRECT FLUORINATION * 321 GENERAL REMARKS ON DIRECT FLUORINATION TECHNIQUES * 321 DIRECT FLUORINATION TECHNIQUES USING ELEMENTAL F 2 * 323 FLUORINATION USING HIGH-VALENT METAL FLUORIDES * 324 SELECTIVE RADICAL FLUORINATION WITH ELECTROPHILIC FLUORINATING AGENTS * 326 XIV * * CONTENTS 13.2.5 13.3 13.3.1 13.3.2 13.3.3 STUDY QUESTIONS ----- 329 ELECTROCHEMICAL FLUORINATION TECHNIQUES ----- 330 CONDITIONS AND SUBSTRATES -----330 CYCLIZATION OF CARBONYL COMPOUNDS ----- 331 ELECTROCHEMICAL FLUORINATION OF HETEROATOM-CONTAINING SUBSTRATES ----- 331 13.3.4 13.4 13.4.1 13.4.2 13.4.3 13.4.4 13.4.5 13.4.6 13.4.7 13.4.8 13.4.9 13.4.10 13.4.11 13.4.12 13.4.13 13.5 13.5.1 13.5.2 13.5.3 13.5.4 13.5.5 13.5.6 13.5.7 13.6 13.6.1 13.6.2 13.6.3 13.6.4 13.7 13.7.1 13.7.2 13.7.3 13.7.4 STUDY QUESTIONS ----- 331 NUCLEOPHILIC SUBSTITUTION -----332 HALOGEN EXCHANGE -----332 DEOXYFLUORINATION OF ALCOHOLS ----- 338 CLEAVAGE OF ETHERS AND EPOXIDES ----- 346 DEOXYFLUORINATION OF CARBONYL COMPOUNDS ----- 350 DEOXYFLUORINATION OF CARBOXYLIC ACIDS AND THEIR DERIVATIVES ----- 354 SULPHUR REPLACEMENT ----- 358 NITROGEN REPLACEMENT * 362 HYDROFLUORINATION OF UNSATURATED C-C BONDS ----- 364 HALOFLUORINATION OF UNSATURATED C-C BONDS ----- 366 FLUOROCARBENE ADDITION TO UNSATURATED C-C BONDS ----- 369 HALO- AND HYDROFLUORINATION OF HIGHLY FLUORINATED OLEFINS ----- 370 HIGHLY FLUORINATED OLEFINS AS BUILDING BLOCKS ----- 372 STUDY QUESTIONS ----- 375 ELECTROPHILIC FLUORINATION -----376 ELEMENTAL FLUORINE AS ELECTROPHILIC FLUORINATING AGENT * 377 ELECTROPHILIC FLUORINATION USING FLUOROXY COMPOUNDS ----- 377 ELECTROPHILIC FLUORINATION USING PERCHLORYL FLUORIDE ----- 380 FLUORAZA COMPOUNDS AS ELECTROPHILIC FLUORINATING AGENTS ----- 381 ASYMMETRIC FLUORINATION USING FLUORAZA REAGENTS * 384 XENON DIFLUORIDE ---- 387 STUDY QUESTIONS ----- 388 METAL-MEDIATED REACTIONS, INCLUDING PHOTOCATALYSIS ----- 388 C-H FLUORINATION ----- 389 FLUOROFUNCTIONALIZATION OF OLEFINS -----397 ALLYLIC, BENZYLIC AND PROPARGYLIC SUBSTRATES WITH A LEAVING GROUP ----- 399 STUDY QUESTIONS ----- 401 SELECTED TRANSFORMATIONS OF FLUORINATED COMPOUNDS ----- 401 REDUCTIVE TRANSFORMATIONS ----- 402 OXIDATIVE TRANSFORMATIONS * 407 HALOGENATIONS ----- 412 STUDY QUESTIONS ----- 414 14 FLUORINATION OF (HETERO-) AROMATIC COMPOUNDS * 415 14.1 ELECTROCHEMICAL FLUORINATION TECHNIQUES ----- 415 CONTENTS XV 14.2 NUCLEOPHILIC SUBSTITUTION ------ 416 14.2.1 HALOGEN EXCHANGE ----- 416 14.2.2 FLUORODENITRATION AND FLUORODESULPHONYLATION * 417 14.2.3 PREPARATION OF PENTAFLUOROPHENYL COMPOUNDS * 418 14.2.4 DEOXYFLUORINATION ----- 420 14.2.5 NITROGEN REPLACEMENT ----- 422 14.2.6 MISCELLANEOUS TRANSFORMATIONS ----- 424 14.2.7 STUDY QUESTIONS ----- 425 14.3 ELECTROPHILIC FLUORINATION ------ 425 14.3.1 ELEMENTAL FLUORINE AS ELECTROPHILIC FLUORINATING AGENT * 425 14.3.2 ELECTROPHILIC FLUORINATION USING FLUOROOXY REAGENTS * 426 14.3.3 XENON DIFLUORIDE AS A SOURCE OF ELECTROPHILIC FLUORINE * 428 14.3.4 ELECTROPHILIC FLUORINATION USING FLUORAZA REAGENTS * 428 14.3.5 STUDY QUESTIONS ----- 430 14.4 REDUCTIVE AROMATIZATION * 430 14.5 METAL-MEDIATED REACTIONS * 430 14.5.1 REACTIONS MEDIATED BY PALLADIUM * 431 14.5.2 REACTIONS MEDIATED BY COPPER * 438 14.5.3 REACTIONS MEDIATED BY SILVER * 441 14.5.4 REACTIONS MEDIATED BY BISMUTH * 441 14.5.5 STUDY QUESTIONS ----- 442 14.6 C-F BOND ACTIVATION ----- 443 14.6.1 REPLACEMENT OF FLUORIDE SUBSTITUENTS IN HIGHLY FLUORINATED AROMATICS * 443 14.6.2 FLUORIDE REPLACEMENT BY MAIN-GROUP ORGANOMETALLICS * 444 14.6.3 C-F BOND ACTIVATION BY TRANSITION METAL COMPLEXES * 446 14.6.4 STUDY QUESTIONS ----- 451 15 PREPARATION OF FLUORINATED OLEFINS AND ACETYLENES * 453 15.1 ELIMINATION REACTIONS * 453 15.1.1 ELIMINATION OF HX * 454 15.1.2 ELIMINATION OF HF * 454 15.1.3 ELIMINATION OF HALOGENS * 455 15.1.4 ELIMINATION OF OTHER SMALL MOLECULES * 457 15.1.5 PYROLYSIS OF FLUORINATED COMPOUNDS * 457 15.1.6 PREPARATION OF FLUORINE-CONTAINING POLYENES * 458 15.1.7 FLUORINATED ACETYLENES * 460 15.1.8 STUDY QUESTIONS * 460 15.2 NUCLEOPHILIC SUBSTITUTION * 461 15.2.1 NUCLEOPHILIC ATTACK ON CF 3 -SUBSTITUTED VINYL COMPOUNDS * 461 15.2.2 ADDITION-ELIMINATION REACTIONS OF FLUORINATED OLEFINS * 462 15.2.3 MISCELLANEOUS REACTIONS TOWARD FLUOROOLEFINS * 463 XVI * - CONTENTS BIBLIOGRAPHY ----- 537 15.2.4 15.3 15.3.1 15.3.2 STUDY QUESTIONS ----- 464 ELECTROPHILIC FLUORINATION ----- 464 FLUORINATION OF VINYL LITHIUM INTERMEDIATES ----- 464 ELECTROPHILIC FLUORINATION OF SUBSTITUTED CYCLOPROPANES AND ALLENES ----- 464 15.3.3 15.3.4 15.4 15.4.1 15.4.2 15.4.3 15.4.4 15.5 15.5.1 MISCELLANEOUS TRANSFORMATIONS ----- 465 STUDY QUESTIONS ----- 465 TRANSITION METAL-FREE INTRODUCTION OF FLUORINATED FRAGMENTS * 466 WITTIG OLEFINATION ----- 466 JULIA- AND JULIA-KOCIENSKI-TYPE OLEFINATIONS ----- 469 HORNER-WADSWORTH-EMMONS OLEFINATION ----- 469 STUDY QUESTIONS -----470 OLEFIN METATHESIS -----470 GENERAL ASPECTS ABOUT METATHESIS REACTIONS OF FLUORINATED OLEFINS ----- 470 15.5.2 15.5.3 15.5.4 15.6 15.6.1 15.6.2 15.6.3 15.6.4 15.6.5 PREPARATION OF FLUORINATED CARBOCYCLES * 471 PREPARATION OF FLUORINATED HETEROCYCLES * 472 STUDY QUESTIONS ----- 472 METAL-MEDIATED REACTIONS, INCLUDING PHOTOCATALYSIS -----474 HYDROFLUORINATION OF ALKYNES * 474 DIRECTED C-H FLUORINATION OF VINYLIC SUBSTRATES ----- 474 FLUORINATION OF VINYL BORONIC ACIDS AND VINYL STANNANES ----- 475 MISCELLANEOUS TRANSFORMATIONS TOWARD MONOFLUOROOLEFINS * 475 PREPARATION OF GEMINAL DIFLUOROOLEFINS FROM CF 3 -SUBSTITUTED ALKENES ----- 475 15.6.6 15.6.7 15.7 PREPARATION OF GEMINAL DIFLUOROOLEFINS FROM DIAZOCOMPOUNDS ----- 476 STUDY QUESTIONS -----476 SELECTIVE HYDRODEFLUORINATION OF HIGHLY FLUORINATED OLEFINS ----- 477 16 SOLUTIONS TO STUDY QUESTIONS -----479 INDEX * 617
adam_txt	CONTENTS PREFACE * V FOREWORD * VII PART A: INTRODUCTION TO FLUORINE CHEMISTRY 1 1.1 1.2 1.3 1.4 SOURCES OF FLUORINE IN NATURE * 5 THE FLUOROSPHERE * 5 FLUORIDE SOURCES AND ELEMENTAL FLUORINE IN MINERALS * 5 NATURAL ORGANOFLUORINE COMPOUNDS * 7 STUDY QUESTIONS * 8 2 2.1 2.2 2.3 2.4 2.5 ELEMENTAL FLUORINE * 9 PROPERTIES AND GENERAL REACTIVITY * 9 POLYFLUORIDE ANIONS * 11 PREPARATION OF F 2 * 11 WORKING WITH ELEMENTAL FLUORINE AND FLUORINATED COMPOUNDS * 13 STUDY QUESTIONS * 14 3 3.1 3.2 3.3 3.4 3.5 3.6 3.7 HYDROGEN FLUORIDE * 15 PREPARATION, GENERAL PROPERTIES AND APPLICATIONS * 15 STRUCTURAL PROPERTIES * 15 ANHYDROUS AND AQUEOUS HYDROGEN FLUORIDE * 16 SALTS OF HYDROGEN FLUORIDE * 17 NAKED FLUORIDE AND LIGAND PROPERTIES * 18 ANHYDROUS HYDROGEN FLUORIDE AS REACTION MEDIUM * 19 STUDY QUESTIONS * 21 4 4.1 4.2 4.3 4.4 PREPARATION OF FLUORINATED COMPOUNDS * 23 TRANSFORMATIONS WITH GASEOUS FLUORINATING AGENTS * 23 SOLID-STATE REACTIONS AND FLUORINATIONS IN FLUX * 27 FLUORINATION IN SOLUTION PHASE * 27 STUDY QUESTIONS * 28 5 5.1 5.2 5.3 COMMON SOLID-STATE STRUCTURES OF INORGANIC FLUORIDES * 31 BINARY FLUORIDES * 31 TERNARY AND QUATERNARY FLUORIDES * 33 STUDY QUESTIONS * 33 X ---- * CONTENTS 6 PROPERTIES OF FLUORINATED COMPOUNDS * 35 7 7.1 7.2 7.3 7.4 HEALTH AND ENVIRONMENTAL ASPECTS OF FLUORINATED COMPOUNDS * 37 IMPACT OF FLUORINATED COMPOUNDS ON HUMANS AND ANIMALS ----- 37 FLUORINATED COMPOUNDS IN THE ENVIRONMENT ----- 38 PERSPECTIVES IN THE USE OF FLUORINATED COMPOUNDS * 41 STUDY QUESTIONS ----- 42 8 8.1 8.2 8.3 8.4 19 F-NMR - AN IMPORTANT ANALYTICAL TOOL FOR FLUORINE CHEMISTS * 43 GENERAL ASPECTS AND REFERENCE SUBSTANCES -----43 CHEMICAL SHIFTS -----44 COUPLING CONSTANTS ----- 47 STUDY QUESTIONS ----- 48 PART B: INORGANIC FLUORINE CHEMISTRY 9 9.1 9.1.1 9.1.2 9.2 MAIN GROUP ELEMENT FLUORIDES * 55 GROUP 1: LITHIUM, SODIUM, POTASSIUM, RUBIDIUM, CESIUM ----- 55 THE ALKALI METAL FLUORIDES ----- 55 STUDY QUESTIONS ----- 56 GROUP 2: BERYLLIUM, MAGNESIUM, CALCIUM, STRONTIUM, BARIUM, RADIUM ----- 56 9.2.1 9.2.2 9.2.3 9.3 9.3.1 9.3.2 9.3.3 9.4 9.4.1 9.4.2 9.4.3 9.5 9.5.1 9.5.2 9.5.3 9.6 9.6.1 9.6.2 9.6.3 BERYLLIUM ----- 56 MAGNESIUM, CALCIUM, STRONTIUM, BARIUM AND RADIUM ----- 58 STUDY QUESTIONS ----- 59 GROUP 13: BORON, ALUMINIUM, GALLIUM, INDIUM, THALLIUM ----- 59 BORON ----- 59 ALUMINIUM, GALLIUM, INDIUM, THALLIUM ----- 64 STUDY QUESTIONS ----- 68 GROUP 14: CARBON, SILICON, GERMANIUM, TIN, LEAD * 68 CARBON ----- 68 SILICON, GERMANIUM, TIN, LEAD * 71 STUDY QUESTIONS ----- 79 GROUP 15: NITROGEN, PHOSPHORUS, ARSENIC, ANTIMONY, BISMUTH ----- 80 NITROGEN ----- 80 PHOSPHORUS, ARSENIC, ANTIMONY, BISMUTH ----- 88 STUDY QUESTIONS ----- 98 GROUP 16: OXYGEN, SULPHUR, SELENIUM, TELLURIUM, POLONIUM ----- 98 OXYGEN ----- 98 SULPHUR, SELENIUM, TELLURIUM, POLONIUM ----- 111 STUDY QUESTIONS ----- 129 CONTENTS * XI 9.7 GROUP 17: CHLORINE, BROMINE, IODINE ----- 130 9.7.1 PREPARATION OF THE HALOGEN FLUORIDES * 130 9.7.2 STRUCTURAL PROPERTIES OF THE HALOGEN FLUORIDES * 132 9.7.3 STABILITY OF THE HALOGEN FLUORIDES * 133 9.7.4 REACTIVITY OF THE HALOGEN FLUORIDES * 133 9.7.5 FLUORINATED CATIONS DERIVED FROM THE HALOGEN FLUORIDES * 135 9.7.6 FLUOROHALOGENATE ANIONS * 137 9.7.7 HALOGEN OXYFLUORIDES * 139 9.7.8 STUDY QUESTIONS ----- 146 9.8 GROUP 18: KRYPTON, XENON, RADON * 147 9.8.1 XENON * 147 9.8.2 KRYPTON ----- 157 9.8.3 RADON * 158 9.8.4 STUDY QUESTIONS ----- 159 10 TRANSITION METAL FLUORIDES AND RARE EARTH METAL FLUORIDES * 161 10.1 GROUP 3: SCANDIUM, YTTRIUM, LANTHANUM, ACTINIUM * 161 10.1.1 COMPOUNDSAND PROPERTIES * 161 10.1.2 STUDY QUESTIONS ----- 163 10.2 THE LANTHANIDES * 163 10.2.1 COMPOUNDSAND PROPERTIES ----- 163 10.2.2 STUDY QUESTIONS ----- 167 10.3 THE ACTINIDES * 168 10.3.1 COMPOUNDS AND PROPERTIES * 168 10.3.2 STUDY QUESTIONS * 179 10.4 GROUP 4: TITANIUM, ZIRCONIUM, HAFNIUM * 179 10.4.1 TITANIUM * 179 10.4.2 ZIRCONIUM AND HAFNIUM * 185 10.4.3 STUDY QUESTIONS ----- 189 10.5 GROUP 5: VANADIUM, NIOBIUM, TANTALUM * 189 10.5.1 VANADIUM * 189 10.5.2 NIOBIUM AND TANTALUM * 197 10.5.3 STUDY QUESTIONS * 203 10.6 GROUP 6: CHROMIUM, MOLYBDENUM, TUNGSTEN * 203 10.6.1 CHROMIUM ----- 203 10.6.2 MOLYBDENUM AND TUNGSTEN * 211 10.6.3 STUDY QUESTIONS * 219 10.7 GROUP 7: MANGANESE, TECHNETIUM, RHENIUM * 220 10.7.1 MANGANESE * 220 10.7.2 TECHNETIUM AND RHENIUM * 226 10.7.3 STUDY QUESTIONS * 234 10.8 IRON, COBALT, NICKEL * 235 XII * CONTENTS 10.8.1 10.8.2 10.9 COMPOUNDS AND PROPERTIES * 235 STUDY QUESTIONS ----- 245 THE PLATINUM METALS: RUTHENIUM, OSMIUM, RHODIUM, IRIDIUM, PLATINUM, PALLADIUM ----- 245 10.9.1 10.9.2 10.10 10.10.1 10.10.2 10.10.3 10.10.4 10.11 10.11.1 10.11.2 10.11.3 10.11.4 10.11.5 COMPOUNDS AND PROPERTIES ----- 245 STUDY QUESTIONS ----- 259 GROUP 11: COPPER, SILVER, GOLD ----- 260 COPPER ----- 260 SILVER ----- 264 GOLD ----- 267 STUDY QUESTIONS -----272 GROUP 12: ZINC, CADMIUM, MERCURY ----- 272 ZINC ----- 272 CADMIUM ----- 273 MERCURY ----- 274 ZINC, CADMIUM AND MERCURY IN HIGHER OXIDATION STATES ----- 277 STUDY QUESTIONS ----- 278 PARTC: ORGANIC FLUORINE CHEMISTRY 11 FLUOROORGANIC COMPOUNDS - UNUSUAL PROPERTIES AND VERSATILE APPLICATIONS * 283 11.1 11.1.1 11.1.2 11.1.3 11.1.4 11.1.5 11.1.6 11.2 PHYSICAL PROPERTIES OF FLUOROORGANIC COMPOUNDS * 283 BOILING POINTS AND DIPOLE MOMENTS * 283 SOLVENT PROPERTIES * 284 SURFACE TENSION AND SURFACE ENERGY * 285 LIPOPHILICITY ----- 285 ACIDITY AND BASICITY * 285 STUDY QUESTIONS * 286 CHEMICAL PROPERTIES AND STABILITY OF FLUOROORGANIC COMPOUNDS AND REACTIVE INTERMEDIATES * 287 11.2.1 11.2.2 11.2.3 11.2.4 11.2.5 11.2.6 11.2.7 11.3 11.3.1 11.3.2 FLUORINE AT SP 3 -CARBONS * 287 FLUORINE AT SP 2 -AND SP-CARBONS * 288 FLUORINATED CARBOCATIONS * 289 FLUORINATED CARBANIONS * 290 FLUORINATED RADICALS * 292 FLUORINATED CARBENES * 293 STUDY QUESTIONS ----- 293 APPLICATIONS OF ORGANOFLUORINE COMPOUNDS * 294 VERSATILE USES OF HALO- AND HYDROFLUOROCARBONS * 294 FLUOROPOLYMERS ----- 294 CONTENTS * XIII 11.3.3 11.3.4 11.3.5 11.3.6 11.3.7 11.3.8 11.3.9 FLUORINATED DYES * 295 FLUORINATED LIQUID CRYSTALS * 296 ORGANIC ELECTRONICS * 296 BIOLOGICALLY ACTIVE COMPOUNDS * 297 MEDICINAL DIAGNOSTICS * 298 FURTHER MEDICAL APPLICATIONS * 298 STUDY QUESTIONS * 299 12 12.1 12.1.1 12.1.2 12.1.3 12.2 12.2.1 12.2.2 12.2.3 12.3 12.3.1 12.3.2 12.3.3 12.3.4 12.3.5 12.4 12.4.1 12.4.2 12.4.3 12.5 12.6 GENERAL REACTION TYPES AND REAGENTS FOR THE INTRODUCTION OF FLUORINE * 301 DIRECT FLUORINATION AND RADICAL REACTIONS * 301 ELEMENTAL FLUORINE AND HIGH-VALENT METAL FLUORIDES * 301 RADICAL FLUORINATION USING ELECTROPHILIC FLUORINATING REAGENTS * 302 STUDY QUESTIONS * 302 ELECTROCHEMICAL FLUORINATION * 302 PREREQUISITES * 303 MECHANISTICAL ASPECTS * 303 STUDY QUESTIONS * 304 NUCLEOPHILIC FLUORINATION ----- 304 HF AND ITS COMPLEXES ----- 304 IONIC FLUORIDES * 305 MOLECULAR FLUORIDES * 307 ENZYMATIC FLUORINATION * 312 STUDY QUESTIONS * 312 ELECTROPHILIC FLUORINATION * 312 FLUOROXY COMPOUNDS, PERCHLORYL FLUORIDE AND XENON DIFLUORIDE * 313 FLUORAZA REAGENTS * 313 STUDY QUESTIONS * 316 METAL-MEDIATED REACTIONS, INCLUDING PHOTOCATALYSIS * 316 HYDRODEFLUORINATION AND DEFLUOROFUNCTIONALIZATION * 317 13 13.1 FLUORINATION OF ALIPHATIC SUBSTRATES * 319 GENERAL TRENDS IN THE SYNTHESIS OF ALIPHATIC ORGANOFLUORINE COMPOUNDS * 319 13.1.1 13.1.2 13.1.3 13.2 13.2.1 13.2.2 13.2.3 13.2.4 THE GENERAL FLUORINE EFFECT * 319 THE SPECIAL FLUORINE EFFECT * 320 STUDY QUESTIONS ----- 320 RADICAL REACTIONS AND DIRECT FLUORINATION * 321 GENERAL REMARKS ON DIRECT FLUORINATION TECHNIQUES * 321 DIRECT FLUORINATION TECHNIQUES USING ELEMENTAL F 2 * 323 FLUORINATION USING HIGH-VALENT METAL FLUORIDES * 324 SELECTIVE RADICAL FLUORINATION WITH ELECTROPHILIC FLUORINATING AGENTS * 326 XIV * * CONTENTS 13.2.5 13.3 13.3.1 13.3.2 13.3.3 STUDY QUESTIONS ----- 329 ELECTROCHEMICAL FLUORINATION TECHNIQUES ----- 330 CONDITIONS AND SUBSTRATES -----330 CYCLIZATION OF CARBONYL COMPOUNDS ----- 331 ELECTROCHEMICAL FLUORINATION OF HETEROATOM-CONTAINING SUBSTRATES ----- 331 13.3.4 13.4 13.4.1 13.4.2 13.4.3 13.4.4 13.4.5 13.4.6 13.4.7 13.4.8 13.4.9 13.4.10 13.4.11 13.4.12 13.4.13 13.5 13.5.1 13.5.2 13.5.3 13.5.4 13.5.5 13.5.6 13.5.7 13.6 13.6.1 13.6.2 13.6.3 13.6.4 13.7 13.7.1 13.7.2 13.7.3 13.7.4 STUDY QUESTIONS ----- 331 NUCLEOPHILIC SUBSTITUTION -----332 HALOGEN EXCHANGE -----332 DEOXYFLUORINATION OF ALCOHOLS ----- 338 CLEAVAGE OF ETHERS AND EPOXIDES ----- 346 DEOXYFLUORINATION OF CARBONYL COMPOUNDS ----- 350 DEOXYFLUORINATION OF CARBOXYLIC ACIDS AND THEIR DERIVATIVES ----- 354 SULPHUR REPLACEMENT ----- 358 NITROGEN REPLACEMENT * 362 HYDROFLUORINATION OF UNSATURATED C-C BONDS ----- 364 HALOFLUORINATION OF UNSATURATED C-C BONDS ----- 366 FLUOROCARBENE ADDITION TO UNSATURATED C-C BONDS ----- 369 HALO- AND HYDROFLUORINATION OF HIGHLY FLUORINATED OLEFINS ----- 370 HIGHLY FLUORINATED OLEFINS AS BUILDING BLOCKS ----- 372 STUDY QUESTIONS ----- 375 ELECTROPHILIC FLUORINATION -----376 ELEMENTAL FLUORINE AS ELECTROPHILIC FLUORINATING AGENT * 377 ELECTROPHILIC FLUORINATION USING FLUOROXY COMPOUNDS ----- 377 ELECTROPHILIC FLUORINATION USING PERCHLORYL FLUORIDE ----- 380 FLUORAZA COMPOUNDS AS ELECTROPHILIC FLUORINATING AGENTS ----- 381 ASYMMETRIC FLUORINATION USING FLUORAZA REAGENTS * 384 XENON DIFLUORIDE ---- 387 STUDY QUESTIONS ----- 388 METAL-MEDIATED REACTIONS, INCLUDING PHOTOCATALYSIS ----- 388 C-H FLUORINATION ----- 389 FLUOROFUNCTIONALIZATION OF OLEFINS -----397 ALLYLIC, BENZYLIC AND PROPARGYLIC SUBSTRATES WITH A LEAVING GROUP ----- 399 STUDY QUESTIONS ----- 401 SELECTED TRANSFORMATIONS OF FLUORINATED COMPOUNDS ----- 401 REDUCTIVE TRANSFORMATIONS ----- 402 OXIDATIVE TRANSFORMATIONS * 407 HALOGENATIONS ----- 412 STUDY QUESTIONS ----- 414 14 FLUORINATION OF (HETERO-) AROMATIC COMPOUNDS * 415 14.1 ELECTROCHEMICAL FLUORINATION TECHNIQUES ----- 415 CONTENTS XV 14.2 NUCLEOPHILIC SUBSTITUTION ------ 416 14.2.1 HALOGEN EXCHANGE ----- 416 14.2.2 FLUORODENITRATION AND FLUORODESULPHONYLATION * 417 14.2.3 PREPARATION OF PENTAFLUOROPHENYL COMPOUNDS * 418 14.2.4 DEOXYFLUORINATION ----- 420 14.2.5 NITROGEN REPLACEMENT ----- 422 14.2.6 MISCELLANEOUS TRANSFORMATIONS ----- 424 14.2.7 STUDY QUESTIONS ----- 425 14.3 ELECTROPHILIC FLUORINATION ------ 425 14.3.1 ELEMENTAL FLUORINE AS ELECTROPHILIC FLUORINATING AGENT * 425 14.3.2 ELECTROPHILIC FLUORINATION USING FLUOROOXY REAGENTS * 426 14.3.3 XENON DIFLUORIDE AS A SOURCE OF ELECTROPHILIC FLUORINE * 428 14.3.4 ELECTROPHILIC FLUORINATION USING FLUORAZA REAGENTS * 428 14.3.5 STUDY QUESTIONS ----- 430 14.4 REDUCTIVE AROMATIZATION * 430 14.5 METAL-MEDIATED REACTIONS * 430 14.5.1 REACTIONS MEDIATED BY PALLADIUM * 431 14.5.2 REACTIONS MEDIATED BY COPPER * 438 14.5.3 REACTIONS MEDIATED BY SILVER * 441 14.5.4 REACTIONS MEDIATED BY BISMUTH * 441 14.5.5 STUDY QUESTIONS ----- 442 14.6 C-F BOND ACTIVATION ----- 443 14.6.1 REPLACEMENT OF FLUORIDE SUBSTITUENTS IN HIGHLY FLUORINATED AROMATICS * 443 14.6.2 FLUORIDE REPLACEMENT BY MAIN-GROUP ORGANOMETALLICS * 444 14.6.3 C-F BOND ACTIVATION BY TRANSITION METAL COMPLEXES * 446 14.6.4 STUDY QUESTIONS ----- 451 15 PREPARATION OF FLUORINATED OLEFINS AND ACETYLENES * 453 15.1 ELIMINATION REACTIONS * 453 15.1.1 ELIMINATION OF HX * 454 15.1.2 ELIMINATION OF HF * 454 15.1.3 ELIMINATION OF HALOGENS * 455 15.1.4 ELIMINATION OF OTHER SMALL MOLECULES * 457 15.1.5 PYROLYSIS OF FLUORINATED COMPOUNDS * 457 15.1.6 PREPARATION OF FLUORINE-CONTAINING POLYENES * 458 15.1.7 FLUORINATED ACETYLENES * 460 15.1.8 STUDY QUESTIONS * 460 15.2 NUCLEOPHILIC SUBSTITUTION * 461 15.2.1 NUCLEOPHILIC ATTACK ON CF 3 -SUBSTITUTED VINYL COMPOUNDS * 461 15.2.2 ADDITION-ELIMINATION REACTIONS OF FLUORINATED OLEFINS * 462 15.2.3 MISCELLANEOUS REACTIONS TOWARD FLUOROOLEFINS * 463 XVI * - CONTENTS BIBLIOGRAPHY ----- 537 15.2.4 15.3 15.3.1 15.3.2 STUDY QUESTIONS ----- 464 ELECTROPHILIC FLUORINATION ----- 464 FLUORINATION OF VINYL LITHIUM INTERMEDIATES ----- 464 ELECTROPHILIC FLUORINATION OF SUBSTITUTED CYCLOPROPANES AND ALLENES ----- 464 15.3.3 15.3.4 15.4 15.4.1 15.4.2 15.4.3 15.4.4 15.5 15.5.1 MISCELLANEOUS TRANSFORMATIONS ----- 465 STUDY QUESTIONS ----- 465 TRANSITION METAL-FREE INTRODUCTION OF FLUORINATED FRAGMENTS * 466 WITTIG OLEFINATION ----- 466 JULIA- AND JULIA-KOCIENSKI-TYPE OLEFINATIONS ----- 469 HORNER-WADSWORTH-EMMONS OLEFINATION ----- 469 STUDY QUESTIONS -----470 OLEFIN METATHESIS -----470 GENERAL ASPECTS ABOUT METATHESIS REACTIONS OF FLUORINATED OLEFINS ----- 470 15.5.2 15.5.3 15.5.4 15.6 15.6.1 15.6.2 15.6.3 15.6.4 15.6.5 PREPARATION OF FLUORINATED CARBOCYCLES * 471 PREPARATION OF FLUORINATED HETEROCYCLES * 472 STUDY QUESTIONS ----- 472 METAL-MEDIATED REACTIONS, INCLUDING PHOTOCATALYSIS -----474 HYDROFLUORINATION OF ALKYNES * 474 DIRECTED C-H FLUORINATION OF VINYLIC SUBSTRATES ----- 474 FLUORINATION OF VINYL BORONIC ACIDS AND VINYL STANNANES ----- 475 MISCELLANEOUS TRANSFORMATIONS TOWARD MONOFLUOROOLEFINS * 475 PREPARATION OF GEMINAL DIFLUOROOLEFINS FROM CF 3 -SUBSTITUTED ALKENES ----- 475 15.6.6 15.6.7 15.7 PREPARATION OF GEMINAL DIFLUOROOLEFINS FROM DIAZOCOMPOUNDS ----- 476 STUDY QUESTIONS -----476 SELECTIVE HYDRODEFLUORINATION OF HIGHLY FLUORINATED OLEFINS ----- 477 16 SOLUTIONS TO STUDY QUESTIONS -----479 INDEX * 617
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series2	De Gruyter Graduate
spelling	Haupt, Axel 1974- Verfasser (DE-588)122898842 aut Organic and inorganic fluorine chemistry methods and applications Axel Haupt Berlin ; Boston De Gruyter [2021] © 2021 XVI, 625 Seiten Illustrationen 24 cm x 17 cm txt rdacontent n rdamedia nc rdacarrier De Gruyter Graduate Anorganische Verbindungen (DE-588)4002147-6 gnd rswk-swf Fluororganische Verbindungen (DE-588)4154846-2 gnd rswk-swf Fluorverbindungen (DE-588)4154876-0 gnd rswk-swf Fluoride (DE-588)4154841-3 gnd rswk-swf TB: Textbook Fluororganische Verbindungen (DE-588)4154846-2 s DE-604 Fluoride (DE-588)4154841-3 s Anorganische Verbindungen (DE-588)4002147-6 s Fluorverbindungen (DE-588)4154876-0 s Walter de Gruyter GmbH & Co. KG (DE-588)10095502-2 pbl Erscheint auch als Online-Ausgabe, PDF 978-3-11-065933-7 Erscheint auch als Online-Ausgabe, EPUB 978-3-11-065950-4 X:MVB https://www.degruyter.com/books/9783110659290 Kurzbeschreibung DNB Datenaustausch application/pdf http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=032620672&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA Inhaltsverzeichnis
spellingShingle	Haupt, Axel 1974- Organic and inorganic fluorine chemistry methods and applications Anorganische Verbindungen (DE-588)4002147-6 gnd Fluororganische Verbindungen (DE-588)4154846-2 gnd Fluorverbindungen (DE-588)4154876-0 gnd Fluoride (DE-588)4154841-3 gnd
subject_GND	(DE-588)4002147-6 (DE-588)4154846-2 (DE-588)4154876-0 (DE-588)4154841-3
title	Organic and inorganic fluorine chemistry methods and applications
title_auth	Organic and inorganic fluorine chemistry methods and applications
title_exact_search	Organic and inorganic fluorine chemistry methods and applications
title_exact_search_txtP	Organic and inorganic fluorine chemistry methods and applications
title_full	Organic and inorganic fluorine chemistry methods and applications Axel Haupt
title_fullStr	Organic and inorganic fluorine chemistry methods and applications Axel Haupt
title_full_unstemmed	Organic and inorganic fluorine chemistry methods and applications Axel Haupt
title_short	Organic and inorganic fluorine chemistry
title_sort	organic and inorganic fluorine chemistry methods and applications
title_sub	methods and applications
topic	Anorganische Verbindungen (DE-588)4002147-6 gnd Fluororganische Verbindungen (DE-588)4154846-2 gnd Fluorverbindungen (DE-588)4154876-0 gnd Fluoride (DE-588)4154841-3 gnd
topic_facet	Anorganische Verbindungen Fluororganische Verbindungen Fluorverbindungen Fluoride
url	https://www.degruyter.com/books/9783110659290 http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=032620672&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA
work_keys_str_mv	AT hauptaxel organicandinorganicfluorinechemistrymethodsandapplications AT walterdegruytergmbhcokg organicandinorganicfluorinechemistrymethodsandapplications

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