Efficient Preparations of Fluorine Compounds

Inbunden, Engelska, 2012

AvHerbert W. Roesky,Herbert W. Roesky,Herbert W Roesky

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The definitive guide to creating fluorine-based compounds—and the materials of tomorrowDiscovered 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 FluorineSynthesis Methods for Exotic Inorganic Fluorides with Varied ApplicationsIntroduction of Fluorine into Compounds via Electrophilic and Nucleophilic ReactionsDirect Fluorination of Organic Compounds with Elemental FluorineEfficient Preparations of Bioorganic Fluorine CompoundsAsymmetric Fluorocyclization ReactionsPreparations of Rare Earth Fluorosulfides and OxyfluorosulfidesThe 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.

Produktinformation

Utgivningsdatum2012-12-07
Mått163 x 241 x 28 mm
Vikt826 g
FormatInbunden
SpråkEngelska
Antal sidor484
FörlagJohn Wiley & Sons Inc
MedarbetareSharpless,KarlBarry
ISBN9781118078563

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Foreword xiPreface xiiiContributors xv1 Preparation of Elemental Fluorine 1Karl O. Christe2 Preparation of Highly Active Cesium Fluoride 7Konrad Seppelt3 Preparation of Highly Active Silver Fluoride 9Konrad Seppelt4 A Room-Temperature Non-Irradiative Synthesis of XeF2 11Ulf Breddemann, John R. DeBackere, and Gary J. Schrobilgen5 Efficient Perfluorination of K2B12H12 in Neutral Acetonitrile 16Dmitry V. Peryshkov, Eric V. Bukovsky, and Steven H. Strauss6 Efficient Preparation of the Highly Soluble ortho- and para-C60(CF2C6F5)2 Derivatives 19Igor V. Kuvychko, Bryon W. Larson, Steven H. Strauss, and Olga V. Boltalina7 Synthesis of Cs[1-H-CB11F11] 22Michal Vala¡sek, Filip Šembera, Michael J. Hughes, Ivan Stibor, Zbyn¡ek Janou¡sek, and Josef Michl8 Synthesis of Zero-Valent Trifluoromethyl Chalcogenato Derivatives, [NMe4]ECF3 (E = S, Se, Te), and Related Compounds 26Wieland Tyrra and Silke Kremer9 Synthesis Methods for Exotic Inorganic Fluorides with Varied Applications 35Dayal T. Meshri, N. C. Mathur, and Ritesh R. Jain10 Tris(pentafluorophenyl)borane, B(C6F5)3, a Powerful, Well-Soluble, Nonoxidizing Lewis Acid and the Weakly Coordinating Tetrakis(pentafluorophenyl)borate Anion, [B(C6F5)4]− 60Hermann-Josef Frohn11 Pentafluorophenyldifluoroborane, C6F5BF2, and Pentafluorophenyltrifluorosilane, C6F5SiF3, Versatile Reagents for Fluorine/Pentafluorophenyl Substitution Reactions in Strongly Oxidizing Hypervalent Nonmetal Fluorides 65Hermann-Josef Frohn12 Iodine(III and V) Fluorides: Interesting Fluorinating Agents 72Hermann-Josef Frohn13 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 76Hermann-Josef Frohn14 Preparation of Transition Metal Sulfide Fluorides 79Michael Gerken15 Transition Metal Carbonyl Sulfur Dioxide and Thiazylfluoride Complexes: Reactions at the Metal Center and at the Ligand 82Rudiger Mews16 Cesium, Mercury, and Silver Salts with Sulfur-Nitrogen-Fluorine Anions: Useful Transfer Reagents for NSF Building Blocks 88Rudiger Mews17 Laboratory-Scale Synthesis of Gold Trifluoride and Uranium Hexafluoride 94Thomas M. Klapotke18 Preparation of Transition Metal Fluorides using ClF3 100Ralf Haiges19 Preparation of Fluorine-Containing Molecular Halides and Heteropolar Salts with Elements of Group 15 and Niobium and Tantalum Halides 108Lothar Kolditz20 Fluoro and Fluorohydroxy Complexes of As, Sb, and Sn 117Lothar Kolditz21 Trifluoromethyl Compounds via Electrophilic and Nucleophilic Reactions 121Jeanne M. Shreeve22 Introduction of Fluorine into Compounds via Electrophilic and Nucleophilic Reactions 127Jeanne M. Shreeve23 The "Real" Iodine and Bromine Monofluorides 133Shlomo Rozen24 The Versatile Chemistry of Acetyl Hypofluorite: The First Hypofluorite Not Bonded to a Polyhaloalkyl Group 139Shlomo Rozen25 Direct Fluorination of Organic Compounds with Elemental Fluorine 146Shlomo Rozen26 The Surprising Chemistry of Bromine Trifluoride 154Shlomo Rozen27 Preparation of Silicon- and Sulfur-Based Fluorinated Methane Derivatives as Versatile Fluoromethylation Reagents 173G.K. Surya Prakash and Fang Wang28 Pentafluoroethyl Lithium: Reactions with Carbonyl Compounds and Epoxides 205Olesya Kazakova and Gerd-Volker Roschenthaler29 Synthesis of gamma-Hydroxy-gamma, gamma-difluoromethylenephosphonates 210Olesya Kazakova and Gerd-Volker Roschenthaler30 Synthesis of Pentafluoro-gamma6-sulfanyl-Substituted Acetylenes for Liquid Crystals 214Olesya Kazakova, Maxim Ponomarenko, and Gerd-Volker Roschenthaler31 Delocalized Lipophilic Cations as a Source of Naked Fluoride and Phase-Transfer Catalysts 220Nataliya Kalinovich, Olesya Kazakova, and Gerd-Volker Roschenthaler32 Methyltrifluoropyruvate Imines Possessing N-oxalyl and N-Phosphonoformyl Groups: Precursors to a Variety of Alpha-CF3-Alpha-Amino Acid Derivatives 227Olesya Kazakova and Gerd-Volker Roschenthaler33 Rhodium-Mediated Synthesis of (3,3,3-Trifluoropropyl)trimethoxysilane and (3,3,3-Trifluoropropyl)triphenylsilane 232Falk Wehmeier and Thomas Braun34 Rhodium-Mediated Synthesis of a Tetrafluoropyridyl-2-boronate Ester 235Michael Teltewskoi and Thomas Braun35 Palladium-Mediated Synthesis of 4-Vinyltetrafluoropyridine and 2,3,5,6-Tetrafluoropyridine 237David Breyer and Thomas Braun36 Preparation of Polyfluoroaryl-1,2-difluorovinylsilanes 240Donald J. Burton and Ba V. Nguyen37 Preparation of (Z)-2-iodo-1,2-difluorostyrenes 243Donald J. Burton and Ling Xue38 Preparation of 1,4-Bis(Z-2-iodo-1,2-difluoroethenyl)benzene 246Donald J. Burton and Craig A. Wesolowski39 Stereospecific Carboamidation Route to (Z)-N-Phenyl-2,3-difluoro-3-(triethylsilyl) acrylamide 248Donald J. Burton and Craig A. Wesolowski40 Preparation of 2-Trifluoromethyl-3,3,3-trifluoropropanal 250Donald J. Burton and Donald A. Wiebe41 Synthesis of Tetrafluorocatechol 252Sudharsanam Ramanathan, Dayong Sang, Vivek Kumar, and David M. Lemal42 Preparation of an Unsymmetrical Bis((perfluoroalkyl)sulfonyl)imide 256Darryl D. Desmarteau and Thomas D. Hickman43 Preparation of Perfluoroalkyl Sulfilimines and Sulfoximines 262Emmanuel Magnier44 Preparation of Trifluoromethylsulfonium Salts 266Emmanuel Magnier45 Preparation of Organometallic Fluorides of Main Group and Transition Elements 270Herbert W. Roesky46 Preparation of Pentafluorosulfanyl Carbonyl Compounds 275John T. Welch47 Preparation of Power-Variable Electrophilic Trifluoromethylating Agents, S-(Trifluoromethyl)dibenzothiophenium Salts Series 279Teruo Umemoto48 Synthesis of Fluorine-Containing Heterocycles from alpha,alpha-Dihydropolyfluoroalkylsulfides and Fluorinated Thiocarboxylic Acids Derivatives 290Vadim M. Timoshemko and Yuriy G. Shermolovich49 Synthesis of Octafluorocyclooctatetraene 308John M. Buzby, Aldos C. Barefoot, III, Michael W. Grayston, Evan D. Laganis, Roy F. Waldron, and David M. Lemal50 Preparation of Fluoroolefins 315Moritz F. Kuhnel and Dieter Lentz51 Preparation of Ionic Liquids of Fluorocomplex and Oxofluorocomplex Anions by Fluoroacid–Base Reactions 334Kazuhiko Matsumoto and Rika Hagiwara52 Synthesis of Difluorocyclopropyl Building Blocks: 2,2-Difluorocyclopropylmethanol and 2-(Bromomethyl)-1,1-difluorocyclopropane 338Wei Xu and William R. Dolbier Jr.53 Preparation of 1,1,2,2,9,9,10,10-Octafluoro[2.2]paracyclophane and Perfluoro[2.2]paracyclophane 343William R. Dolbier Jr., Jian-Xi Duan, Alex J. Roche, and Lianhao Zhang54 Synthesis and Application of gem-Difluoromethylenated and Trifluoromethylated Building Blocks 349Feng-Ling Qing and Xiao-Long Qiu55 1,3-Dipolar Cycloaddition Reactions to Fluoroalkenes 365Hanna Wojtowicz-Rajchel and Henryk Koroniak56 Synthesis of Fluorinated Vinyl Derivatives of Nucleic Acid Bases 370Hanna Wojtowicz-Rajchel, Donata Pluskota-Karwatka, and Henryk Koroniak57 Synthesis of CF3-Substituted Aziridine Ring by the Gabriel Reaction 375Tomasz Cytlak, Bartosz Marciniak, and Henryk Koroniak58 Preparation of alpha-Fluoro Amino and alpha-Fluoro Enamino Reagents 379Justyna Walkowiak and Henryk Koroniak59 Synthesis of Original Fluoromonomers and Their Radical Copolymerization with Vinylidene Fluoride 385Bruno Ameduri60 Convergent 18F Radiosynthesis 396V. Gouverneur and O. Lozano61 Asymmetric Fluorocyclization Reactions 400V. Gouverneur and O. Lozano62 Preparation of Allylic Fluorides 405V. Gouverneur and O. Lozano63 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 412Orlin Petrov, Matthias Schneider, Rolf Bohlmann, Stephan Vettel, and Helmut Vorbr¨uggen64 Preparation of Rare Earth Fluorosulfides and Oxyfluorosulfides 415A. Demourgues and A. Tressaud65 Preparation of Carbon-Fluorine Compounds and Fluoride or Oxide Fluoride-Intercalated Graphites 425Tsuyoshi Nakajima66 Safe Synthesis of Superstoichiometric Mesoporous Fluorocarbons 433Valentin N. Mitkin67 Preparation of Fluorinated alpha-Alumina 442Erhard Kemnitz, Toma¡z Skapin, and John M. Winfield68 High-Yield Synthesis of a Single Asymmetric Isomer of C70(CF3)10 by High-Temperature Radical Trifluoromethylation 447Natalia B. Shustova, Steven H. Strauss, and Olga V. BoltalinaIndex 451

“As Prof. K. Barry Sharpless comments in the Foreword, ‘Many years of experience, together with deep and catholic knowledge of chemical reactivity principles, is the important coin in this [fluorine chemistry] realm’, and I would recommend this book to anyone involved in synthetic chemistry interested in laboratory synthesis involving fluorinating reagents or fluorinated molecules as an introduction into the experimental and chemical reactivity possibilities now available.” (ChemMedChem, 1 August 2013)