Efficient preparations of fluorine compounds / ed. by H.W.Roesky. - Hoboken: Wiley, 2013. - xx, 454 p.: ill. (some color). - Incl. bibl. ref. - Ind.: p.451-454. - ISBN 978-1-118-07856-3  Место хранения:   024 | Институт неорганической химии им. А.В.Николаева CO РАН | Новосибирск

Оглавление / Contents

Foreword ....................................................... xi Preface ...................................................... xiii Contributors ................................................... xv 1 Preparation of Elemental Fluorine ............................ 1 Karl O. Christe 2 Preparation of Highly Active Cesium Fluoride ................. 7 Konrad Seppelt 3 Preparation of Highly Active Silver Fluoride ................. 9 Konrad Seppelt 4 A Room-Temperature Non-Irradiative Synthesis of XeF2 ........ 11 Ulf Breddemann, John R. DeBackere, and Gary J. Schrobilgen 5 Efficient Perfluorination of K2BnHi2 in Neutral Acetonitrile ................................................ 16 Dmitry V. Peryshkov, Eric V. Bukovsky, and Steven H. Strauss 6 Efficient Preparation of the Highly Soluble ortho- and para-C60(CF2C6F5)2 Derivatives .............................. 19 Igor V. Kuvychko, Bryon W. Larson, Steven H. Strauss, and Olga V. Boltalina 7 Synthesis of Cs[1-H-CB11F11] ................................ 22 Michal Valásek, Filip Šembera, Michael J. Hughes, Ivan Stibor, Zbynek Janoušek, and Josef Michl 8 Synthesis of Zero-Valent Trifluoromethyl Chalcogenato Derivatives, [NMe4]ECF3 (E = S, Se, Те), and Related Compounds ................................................... 26 Wieland Tyrra and Silke Kremer 9 Synthesis Methods for Exotic Inorganic Fluorides with Varied Applications ......................................... 35 Dayal T. Meshri, N.C. Mathur, and Ritesh R. Jain 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]- ................................................. 60 Hermann-Josef Frohn 11 Pentafluorophenyldifluoroborane, C6F5BF2, and Pentafluorophenyltrifluorosilane, C6F5SiF3, Versatile Reagents for Fluorine/Pentafluorophenyl Substitution Reactions in Strongly Oxidizing Hypervalent Nonmetal Fluorides ................................................... 65 Hermann-Josef Frohn 12 Iodine(III and V) Fluorides: Interesting Fluorinating Agents ...................................................... 72 Hermann-Josef Frohn 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 .................... 76 Hermann-Josef Frohn 14 Preparation of Transition Metal Sulfide Fluorides ........... 79 Michael Gerken 15 Transition Metal Carbonyl Sulfur Dioxide and Thiazylfluoride Complexes: Reactions at the Metal Center and at the Ligand ........................................... 82 Rüdiger Mews 16 Cesium, Mercury, and Silver Salts with Sulfur-Nitrogen- Fluorine Anions: Useful Transfer Reagents for NSF Building Blocks ...................................................... 88 Rьdiger Mews 17 Laboratory-Scale Synthesis of Gold Trifluoride and Uranium Hexafluoride ................................................ 94 Thomas M. Klapötke 18 Preparation of Transition Metal Fluorides using C1F3 ....... 100 Ralf Haiges 19 Preparation of Fluorine-Containing Molecular Halides and Heteropolar Salts with Elements of Group 15 and Niobium and Tantalum Halides ....................................... 108 Lothar Kolditz 20 Fluoro and Fluorohydroxy Complexes of As, Sb, and Sn ....... 117 Lothar Kolditz 21 Trifluoromethyl Compounds via Electrophilic and Nucleophilic Reactions ..................................... 121 Jeanne M. Shreeve 22 Introduction of Fluorine into Compounds via Electrophilic and Nucleophilic Reactions ................................. 127 Jeanne M. Shreeve 23 The "Real" Iodine and Bromine Monofluorides ................ 133 Shlomo Rozen 24 The Versatile Chemistry of Acetyl Hypofluorite: The First Hypofluorite Not Bonded to a Polyhaloalkyl Group ........... 139 Shlomo Rozen 25 Direct Fluorination of Organic Compounds with Elemental Fluorine ................................................... Shlomo Rozen 26 The Surprising Chemistry of Bromine Trifluoride ............ 154 Shlomo Rozen 27 Preparation of Silicon- and Sulfur-Based Fluorinated Methane Derivatives as Versatile Fluoromethylation Reagents ................................................... 173 G.K. Surya Prakash and Fang Wang 28 Pentafluoroethyl Lithium: Reactions with Carbonyl Compounds and Epoxides ..................................... 205 Olesya Kazakova and Gerd-Volker Röschenthaler 29 Synthesis of γ-Hydroxy-α,α-difluoromethylenephosphonates ... 210 Olesya Kazakova and Gerd-Volker Röschenthaler 30 Synthesis of Pentafluoro-λ6-sulfanyl-Substituted Acetylenes for Liquid Crystals ............................. 214 Olesya Kazakova, Maxim Ponomarenko, and Gerd-Volker Röschenthaler 31 Delocalized Lipophilic Cations as a Source of Naked Fluoride and Phase-Transfer Catalysts ...................... 220 Nataliya Kalinovich, Olesya Kazakova, and Gerd-Volker Röschenthaler 32 Methyltrifluoropyruvate Imines Possessing N-oxalyl and N-Phosphonoformyl Groups: Precursors to a Variety of α-CF3-α-Amino Acid Derivatives ............................. 227 Olesya Kazakova and Gerd-Volker Röschenthaler 33 Rhodium-Mediated Synthesis of (3,3,3-Trifluoropropyl) trimethoxysilane and (3,3,3-Trifluoropropyl) triphenylsilane ............................................ 232 Falk Wehmeier and Thomas Braun 34 Rhodium-Mediated Synthesis of a Tetrafluoropyridyl-2- boronate Ester ............................................. 235 Michael Teltewskoi and Thomas Braun 35 Palladium-Mediated Synthesis of 4-Vinyltetrafluoropyridine and 2,3,5,6-Tetrafluoropyridine ............................ 237 David Brey er and Thomas Braun 36 Preparation of Polyfluoroaryl-1,2-difluorovinylsilanes ..... 240 Donald J. Burton and Ba V. Nguyen 37 Preparation of (Z)-2-iodo-1,2-difluorostyrenes ............. 243 Donald J. Burton and Ling Xue 38 Preparation of l,4-Bis(Z-2-iodo-1,2-difluoroethenyl) benzene .................................................... 246 Donald J. Burton and Craig A. Wesolowski 39 Stereospecific Carboamidation Route to (Z)-N-Phenyl-2,3- difluoro-3-(triethylsilyl) acrylamide ...................... 248 Donald J. Burton and Craig A. Wesolowski 40 Preparation of 2-Trifluoromethyl-3,3,3-trifluoropropanal ... 250 Donald J. Burton and Donald A. Wiebe 41 Synthesis of Tetrafluorocatechol ........................... 252 Sudharsanam Ramanathan, Dayong Sang, Vivek Kumar, and David M. Lemal 42 Preparation of an Unsymmetrical Bis((perfluoroalkyl) sulfonyl)imide ............................................. 256 Darryl D. Desmarteau and Thomas D. Hickman 43 Preparation of Perfluoroalkyl Sulfilimines and Sulfoximines ............................................... 262 Emmanuel Magnier 44 Preparation of Trifluoromethylsulfonium Salts .............. 266 Emmanuel Magnier 45 Preparation of Organometallic Fluorides of Main Group and Transition Elements ........................................ 270 Herbert W. Roesky 46 Preparation of Pentafluorosulfanyl Carbonyl Compounds ...... 275 John T. Welch 47 Preparation of Power-Variable Electrophilic Trifluoromethylating Agents, S-(TrifluoromethyI) dibenzothiophenium Salts Series ............................ 279 Teruo Umemoto 48 Synthesis of Fluorine-Containing Heterocycles from a,a- Dihydropolyfluoroalkylsulfides and Fluorinated Thiocarboxylic Acids Derivatives ........................... 290 Vadim M. Timoshemko and Yuriy G. Shermolovich 49 Synthesis of Octafluorocyclooctatetraene ................... 308 John M. Buzby, Aldos С. Barefoot, III, Michael W. Grayston, Evan D. Laganis, Roy F. Waldron, and David M. Lemal 50 Preparation of Fluoroolefins ............................... 315 Moritz F. Kühnel and Dieter Lentz 51 Preparation of Ionic Liquids of Fluorocomplex and Oxofluorocomplex Anions by Fluoroacid-Base Reactions ....... 334 Kazuhiko Matsumoto and Rika Hagiwara 52 Synthesis of Difluorocyclopropyl Building Blocks: 2,2- DifluorocyclopropylmethanoI and 2-(Bromomethyl)-l,l- difluorocyclopropane ....................................... 338 Wei Xu and William R. Dolbier Jr. 53 Preparation of l,l,2,2,9,9,10,10-Octafluoro[2.2] paracyclophane and Perfluoro[2.2]paracyclophane ............ 343 William R. Dolbier Jr., Jian-Xi Duan, Alex J. Roche, and Lianhao Zhang 54 Synthesis and Application of gem-Difluoromethylenated and Trifluoromethylated Building Blocks ........................ 349 Feng-Ling Qing and Xiao-Long Qiu 55 1,3-Dipolar Cycloaddition Reactions to Fluoroalkenes ....... 365 Hanna Wójtowicz-Rajchel and Henryk Koroniak 56 Synthesis of Fluorinated Vinyl Derivatives of Nucleic Acid Bases ................................................. 370 Hanna Wójtowicz-Rajchel, Donata Pluskota-Karwatka, and Henryk Koroniak 57 Synthesis of CF3-Substituted Aziridine Ring by the Gabriel Reaction ........................................... 375 Tomasz Cytlak, Bartosz Marciniak, and Henryk Koroniak 58 Preparation of α-Fluoro Amino and α-Fluoro Enamino Reagents ................................................... 379 Justyna Walkowiak and Henryk Koroniak 59 Synthesis of Original Fluoromonomers and Their Radical Copolymerization with Vinylidene Fluoride .................. 385 Bruno Ameduri 60 Convergent 18F Radiosynthesis .............................. 396 V. Gouverneur and O. Lozano 61 Asymmetric Fluorocyclization Reactions ..................... 400 V. Gouverneur and O. Lozano 62 Preparation of Allylic Fluorides ........................... 405 V. Gouverneur and O. Lozano 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 ................................................ 412 Orlin Petrov, Matthias Schneider, Rolf Bohlmann, Stephan Vettel, and Helmut Vorbrьggen 64 Preparation of Rare Earth Fluorosulfides and Oxyfluorosulfides .......................................... 415 A. Demourgues and A. Tressaud 65 Preparation of Carbon-Fluorine Compounds and Fluoride or Oxide Fluoride-Intercalated Graphites ...................... 425 Tsuyoshi Nakajima 66 Safe Synthesis of Superstoichiometric Mesoporous Fluorocarbons .............................................. 433 Valentin N. Mitkin 67 Preparation of Fluorinated γ-Alumina ....................... 442 Erhard Kemnitz, Tomaz Skapin, and John M. Winfield 68 High-Yield Synthesis of a Single Asymmetric Isomer of C70(CF3)10 by High-Temperature Radical Trifluoromethylation ....................................... 447 Natalia B. Shustova, Steven H. Strauss, and Olga V. Boltalina Index ......................................................... 451