Description
The definitive guide to creating fluorine-based compounds—and the materials of tomorrow
Discovered as an element by the French chemist Henri Moissan in 1886, through electrolysis of potassium fluoride in anhydrous hydrogen fluoride—"le fluor," or fluorine, began its chemical history as a substance both elusive and dangerous. With a slight pale yellow hue, fluorine is at room temperature a poisonous diatomic gas. Resembling a spirit from a chemical netherworld, fluorine is highly reactive, difficult to handle, yet very versatile as a reagent—with the power to form compounds with almost any other element.
Comprising 20% of pharmaceutical products and 30% of agrochemical compounds, as well as playing a key role in electric cars, electronic devices, and space technology, compounds containing fluorine have grown in importance across the globe. Learning how to safely handle fluorine in the preparation of innovative new materials—with valuable new properties—is of critical importance to chemists today. Bringing together the research and methods of leading scientists in the fluorine field, Efficient Preparations of Fluorine Compounds is the definitive manual to creating, and understanding the reaction mechanisms integral to a wide variety of fluorine compounds. With sixty-eight contributed chapters, the book's extensive coverage includes:
- Preparation of Elemental Fluorine
- Synthesis Methods for Exotic Inorganic Fluorides with Varied Applications
- Introduction of Fluorine into Compounds via Electrophilic and Nucleophilic Reactions
- Direct Fluorination of Organic Compounds with Elemental Fluorine
- Efficient Preparations of Bioorganic Fluorine Compounds
- Asymmetric Fluorocyclization Reactions
- Preparations of Rare Earth Fluorosulfides and Oxyfluorosulfides
The book offers methods and results that can be reproduced by students involved in advanced studies, as well as practicing chemists, pharmaceutical scientists, biologists, and environmental researchers. The only chemical resource of its kind, Efficient Preparations of Fluorine Compounds—from its first experiment to its last—is a unique window into the centuries old science of fluorine and the limitless universe of fluorine-based compounds.
Chapter
CHAPTER 4 A Room-Temperature Non-Irradiative Synthesis of XeF2
pp.：
31 – 33
CHAPTER 5 Efficient Perfluorination of K2B12H12 in Neutral Acetonitrile
pp.：
33 – 38
CHAPTER 6 Efficient Preparation of the Highly Soluble ortho- and para-C60(CF2C6F5)2 Derivatives
pp.：
38 – 41
CHAPTER 7 Synthesis of Cs[1-H-CB11F11]
pp.：
41 – 44
CHAPTER 8 Synthesis of Zero-Valent Trifluoromethyl Chalcogenato Derivatives, [NMe4]ECF3 (E = S, Se, Te), and Related Compounds
pp.：
44 – 48
CHAPTER 9 Synthesis Methods for Exotic Inorganic Fluorides with Varied Applications
pp.：
48 – 57
CHAPTER 10 Tris(pentafluorophenyl)borane, B(C6F5)3, a Powerful, Well-Soluble, Nonoxidizing Lewis Acid and the Weakly Coordinating Tetrakis(pentafluorophenyl)borate Anion, [B(C6F5)4]-
pp.：
57 – 82
CHAPTER 11 Pentafluorophenyldifluoroborane, C6F5BF2, and Pentafluorophenyltrifluorosilane, C6F5SiF3, Versatile Reagents for Fluorine/Pentafluorophenyl Substitution Reactions in Strongly Oxidizing Hypervalent Nonmetal Fluorides
pp.：
82 – 87
CHAPTER 12 Iodine(III and V) Fluorides: Interesting Fluorinating Agents
pp.：
87 – 94
CHAPTER 13 Tetramethylammonium Fluoride, [N(CH3)4]F, a Widely Applicable Reagent to Introduce Fluoride Ions and a Suitable Nucleophile to Initiate the Transfer of Perfluoroorganyl Groups to Electrophiles
pp.：
94 – 98
CHAPTER 14 Preparation of Transition Metal Sulfide Fluorides
pp.：
98 – 101
CHAPTER 15 Transition Metal Carbonyl Sulfur Dioxide and Thiazylfluoride Complexes: Reactions at the Metal Center and at the Ligand
pp.：
101 – 104
CHAPTER 16 Cesium, Mercury, and Silver Salts with Sulfur–Nitrogen–Fluorine Anions: Useful Transfer Reagents for NSF Building Blocks
pp.：
104 – 110
CHAPTER 17 Laboratory-Scale Synthesis of Gold Trifluoride and Uranium Hexafluoride
pp.：
110 – 116
CHAPTER 18 Preparation of Transition Metal Fluorides using ClF3
pp.：
116 – 122
CHAPTER 19 Preparation of Fluorine-Containing Molecular Halides and Heteropolar Salts with Elements of Group 15 and Niobium and Tantalum Halides
pp.：
122 – 130
CHAPTER 20 Fluoro and Fluorohydroxy Complexes of As, Sb, and Sn
pp.：
130 – 139
CHAPTER 21 Trifluoromethyl Compounds via Electrophilic and Nucleophilic Reactions
pp.：
139 – 143
CHAPTER 22 Introduction of Fluorine into Compounds via Electrophilic and Nucleophilic Reactions
pp.：
143 – 149
CHAPTER 23 The “Real” Iodine and Bromine Monofluorides
pp.：
149 – 155
CHAPTER 24 The Versatile Chemistry of Acetyl Hypofluorite: The First Hypofluorite Not Bonded to a Polyhaloalkyl Group
pp.：
155 – 161
CHAPTER 25 Direct Fluorination of Organic Compounds with Elemental Fluorine
pp.：
161 – 168
CHAPTER 26 The Surprising Chemistry of Bromine Trifluoride
pp.：
168 – 176
CHAPTER 27 Preparation of Silicon- and Sulfur-Based Fluorinated Methane Derivatives as Versatile Fluoromethylation Reagents
pp.：
176 – 195
CHAPTER 28 Pentafluoroethyl Lithium: Reactions with Carbonyl Compounds and Epoxides
pp.：
195 – 227
CHAPTER 29 Synthesis of -Hydroxy- , - difluoromethylenephosphonates
pp.：
227 – 232
CHAPTER 30 Synthesis of Pentafluoro- 6-sulfanyl- Substituted Acetylenes for Liquid Crystals
pp.：
232 – 236
CHAPTER 31 Delocalized Lipophilic Cations as a Source of Naked Fluoride and Phase-Transfer Catalysts
pp.：
236 – 242
CHAPTER 32 Methyltrifluoropyruvate Imines Possessing N-oxalyl and N-Phosphonoformyl Groups: Precursors to a Variety of -CF3- -Amino Acid Derivatives
pp.：
242 – 249
CHAPTER 33 Rhodium-Mediated Synthesis of (3,3,3- Trifluoropropyl)trimethoxysilane and (3,3,3-Trifluoropropyl)triphenylsilane
pp.：
249 – 254
CHAPTER 34 Rhodium-Mediated Synthesis of a Tetrafluoropyridyl-2-boronate Ester
pp.：
254 – 257
CHAPTER 35 Palladium-Mediated Synthesis of 4-Vinyltetrafluoropyridine and 2,3,5,6-Tetrafluoropyridine
pp.：
257 – 259
CHAPTER 36 Preparation of Polyfluoroaryl- 1,2-difluorovinylsilanes
pp.：
259 – 262
CHAPTER 37 Preparation of ( Z)-2-iodo-1,2-difluorostyrenes
pp.：
262 – 265
CHAPTER 38 Preparation of 1,4-Bis( Z-2-iodo-1,2- difluoroethenyl)benzene
pp.：
265 – 268
CHAPTER 39 Stereospecific Carboamidation Route to ( Z)- N-Phenyl-2,3-difluoro-3- (triethylsilyl) acrylamide
pp.：
268 – 270
CHAPTER 40 Preparation of 2-Trifluoromethyl- 3,3,3-trifluoropropanal
pp.：
270 – 272
CHAPTER 41 Synthesis of Tetrafluorocatechol
pp.：
272 – 274
CHAPTER 42 Preparation of an Unsymmetrical Bis((perfluoroalkyl)sulfonyl)imide
pp.：
274 – 278
CHAPTER 43 Preparation of Perfluoroalkyl Sulfilimines and Sulfoximines
pp.：
278 – 284
CHAPTER 44 Preparation of Trifluoromethylsulfonium Salts
pp.：
284 – 288
CHAPTER 45 Preparation of Organometallic Fluorides of Main Group and Transition Elements
pp.：
288 – 292
CHAPTER 46 Preparation of Pentafluorosulfanyl Carbonyl Compounds
pp.：
292 – 297
CHAPTER 47 Preparation of Power-Variable Electrophilic Trifluoromethylating Agents, S-(Trifluoromethyl) dibenzothiophenium Salts Series
pp.：
297 – 301
CHAPTER 48 Synthesis of Fluorine-Containing Heterocycles from , -Dihydropolyfluoroalkylsulfides and Fluorinated Thiocarboxylic Acids Derivatives
pp.：
301 – 312
CHAPTER 49 Synthesis of Octafluorocyclooctatetraene
pp.：
312 – 330
CHAPTER 50 Preparation of Fluoroolefins
pp.：
330 – 337
CHAPTER 51 Preparation of Ionic Liquids of Fluorocomplex and Oxofluorocomplex Anions by Fluoroacid–Base Reactions
pp.：
337 – 356
CHAPTER 52 Synthesis of Difluorocyclopropyl Building Blocks: 2,2-Difluorocyclopropylmethanol and 2-(Bromomethyl)-1,1- difluorocyclopropane
pp.：
356 – 360
CHAPTER 53 Preparation of 1,1,2,2,9,9,10, 10-Octafluoro[2.2]paracyclophane and Perfluoro[2.2]paracyclophane
pp.：
360 – 365
CHAPTER 54 Synthesis and Application of gem-Difluoromethylenated and Trifluoromethylated Building Blocks
pp.：
365 – 371
CHAPTER 55 1,3-Dipolar Cycloaddition Reactions to Fluoroalkenes
pp.：
371 – 387
CHAPTER 56 Synthesis of Fluorinated Vinyl Derivatives of Nucleic Acid Bases
pp.：
387 – 392
CHAPTER 57 Synthesis of CF3-Substituted Aziridine Ring by the Gabriel Reaction
pp.：
392 – 397
CHAPTER 58 Preparation of -Fluoro Amino and -Fluoro Enamino Reagents
pp.：
397 – 401
CHAPTER 59 Synthesis of Original Fluoromonomers and Their Radical Copolymerization with Vinylidene Fluoride
pp.：
401 – 407
CHAPTER 60 Convergent 18F Radiosynthesis
pp.：
407 – 418
CHAPTER 61 Asymmetric Fluorocyclization Reactions
pp.：
418 – 422
CHAPTER 62 Preparation of Allylic Fluorides
pp.：
422 – 427
CHAPTER 63 Dehydroxyfluorinations of Primary or Secondary Alcohols Using Perfluoro n-Butylsulfonyl Fluoride (Nonaflyl Fluoride) in Combination with 1,8-Diaza-bicyclo[5.4.0]undec-7-ene
pp.：
427 – 434
CHAPTER 64 Preparation of Rare Earth Fluorosulfides and Oxyfluorosulfides
pp.：
434 – 437
CHAPTER 65 Preparation of Carbon–Fluorine Compounds and Fluoride or Oxide Fluoride-Intercalated Graphites
pp.：
437 – 447
CHAPTER 66 Safe Synthesis of Superstoichiometric Mesoporous Fluorocarbons
pp.：
447 – 455
CHAPTER 67 Preparation of Fluorinated -Alumina
pp.：
455 – 464
CHAPTER 68 High-Yield Synthesis of a Single Asymmetric Isomer of C70(CF3)10 by High-Temperature Radical Trifluoromethylation
pp.：
464 – 469
Supplemental Images
pp.：
473 – 477
Efficient Preparations of Fluorine Compounds
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