Efficient Preparation of Fluorine Compounds Book

Foreword

Preface

Contributors

1 Preparation of Elemental Fluorine
Karl O. Christe

2 Preparation of Highly Active Caesium Fluoride
Konrad Seppelt

3 Preparation of Highly Active Silver Fluoride
Konrad Seppelt

4 A Room Temperature, Non-Irradiative Synthesis of Xenon Difluoride (XeF2)
Ulf Breddemann, John R. DeBackere, Gary J. Schrobilgen

5 Efficient Perfluorination of K2B12H12 in Neutralizing Acetonitrile
Dmitry V. Peryshkov, Steven H. Strauss

6 Efficient Preparation of the Highly Soluble ortho- and para-C60(CF2C6F5)2 Derivatives
Igor V. Kuvychko, Bryon W. Larson, Steven H. Strauss, and Olga V. Boltalina

7 Synthesis of Cs[1-H-CB11F11]
Josef Michl

8 Synthesis of Zero-Valent Trifluoromethyl Chalcogenato Derivatives, [NMe4]ECF3 (E = S, Se, Te) and Related Compounds
Wieland Tyrra, Silke Kremer

9 Synthesis Methods for Exotic Inorganic Fluorides with Varied Applications
Dayal T. Meshri, N. C. Mathur, Ritesh R. Jain

10 Tris(pentafluorophenyl)boran, B(C6F5)3, a Powerful, Well-soluble, and Non-oxidizing Lewis Acid and the Weakly Coordinating Tetrakis(pentafluorophenyl)borate Anion, [B(C6F5)4]?
Hermann-Josef Frohn

11 Pentafluorophenyldifluoroboran, C6F5BF2, and Pentafluorophenyltrifluorosilane, C6F5SiF3, Versatile Reagents for Fluorine/Pentafluorophenyl Substitution Reactions in Strongly Oxidizing Hypervalent Non-metal Fluorides
Hermann-Josef Frohn

12 Iodine(III and V) Fluorides: Interesting Fluorinating Agents
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 Hermann-Josef Frohn

14 Preparation of Transition Metal Sulfide Fluorides
Michael Gerken

15 Transition Metal Carbonyl Sulfur Dioxide and Thiazylfluoride Complexes: Reactions at the Metal Center and at the Ligand
Rüdiger Mews

16 Cesium-, Mercury- and Silver-Salts with Sulfur-Nitrogen-Fluorine Anions: Useful Transfer-Reagents for NSF-Building Blocks
Rüdiger Mews

17 Laboratory-Scale Synthesis of Gold Trifluoride and Uranium Hexafluoride
Thomas M. Klapötke

18 Preparation of Transition Metal Fluorides using ClF3
Ralf Haiges

19 Preparation of Fluorine Containing Molecular Halides and Hetero polar Salts with Elements of Group 15 and Niobium and Tantalum Halides
Lothar Kolditz

20 Fluoro- and Fluorohydroxy Complexes of As, Sb, and Sn
Lothar Kolditz

21 Trifluoromethyl Compounds via Electrophilic and Nucleophilic Reactions
Jeanne M. Shreeve

22 Introduction of Fluorine into Compounds via Electrophilic and Nucleophilic Reactions
Jeanne M. Shreeve

23 The ?Real? Iodine and Bromine Mono-Fluorides
Shlomo Rozen

24 The Versatile Chemistry of Acetyl Hypofluorite—Hypofluorite not Bonded to Polyhaloalkyl group Shlomo Rozen

25 Direct Fluorination of Organic Compounds with Elemental Fluorine
Shlomo Rozen

26 The Surprising Chemistry of Bromine Trifluoride
Shlomo Rozen

27 Preparation of Silicon- and Sulfur-Based Fluorinated Methane Derivatives as Versatile Fluoromethylation Reagents
G. K. Surya Prakash, Fang Wang

28 Pentafluoroethyl Lithium: Reactions with Carbonyl Compounds and Epoxides
Gerd-Volker Röschenthaler

29 Synthesis of ?-hydroxy-α,α-difluoromethylenephosphonates
Gerd-Volker Röschenthaler

30 Synthesis of Pentafluoro-?6-sulfanyl Substituted Acetylenes for Liquid Crystals
Gerd-Volker Röschenthaler

31 Delocalized Lipophilic Cations as a Source of Naked Fluoride and Phase-transfer Catalysts
Gerd-Volker Röschenthaler

32 Methyltrifluoropyruvate Imines Possessing N-oxalyl and N-phosphonoformyl Groups—Precursors to a Variety of α-CF3-α-amino Acid Derivatives
Gerd-Volker Röschenthaler

33 Rhodium-mediated Synthesis of (3,3,3-Trifluoropropyl)trimethoxysilane and (3,3,3 trifluoropropyl)triphenylsilane
Falk Wehmeier, Thomas Braun

34 Rhodium-mediated Synthesis of a Tetrafluoropyridyl-2-boronate Ester
Michael Teltewskoi, Thomas Braun

35 Palladium-mediated Synthesis of 4-Vinyltetrafluoropyridine and 2,3,5,6-Tetrafluoropyridine
David Breyer, Thomas Braun

36 Preparation of Polyfluoroaryl-1,2-difluorovinylsilanes
Donald J. Burton, Ba V. Nguyen

37Preparation of (Z)-2-iodo-1,2-difluorostyrenes
Donald J. Burton, Ling Xue

38 Preparation of 1,4-Bis(Z-2-iodo-1,2-difluoroethenyl)benzene
Donald J. Burton, Craig A. Wesolowski

39Stereospecific Carboamidation Route to (Z)-N-Phenyl-2,3-difluoro-3-(triethylsilyl) acrylamide
Donald J. Burton, Craig A. Wesolowski

40 Preparation of 2-Trifluoromethyl-3,3,3-trifluoropropanal
Donald J. Burton, Donald A. Wiebe

41 Synthesis of Tetrafluorocatechol
Sudharsanam Ramanathan, Dayong Sang, Vivek Kumar, David M. Lemal

42 Preparation of an Unsymmetrial Bis((perfluoroalkyl)sulfonyl)imide
Darryl D. DesMarteau, Thomas D. Hickman

43 Preparation of Perfluoroalkyl Sulfilimines and Sulfoximines
Emmanuel Magnier

44 Preparation of Trifluoromethylsulfonium Salts
Emmanuel Magnier

45 Preparation of Organometallic Fluorides of Main Group and Transition Elements
Herbert W. Roesky

46 Preparation of Pentafluorosulfanyl Carbonyl Compounds
John T. Welch

47 Preparation of Power-variable Electrophilic Trifluoromethylating Agents, S-(Trifluoromethyl)dibenzothiophenium Salts Series
Teruo Umemoto

48 Synthesis of Fluorine Containing Heterocycles from α,α-Dihydropolyfluoroalkylsulfides and Fluorinated Thiocarboxylic Acids
Vadim M. Timoshemko, Yuriy G.Shermolovich

49 Synthesis of Octafluorocyclooctatetraene
John M. Buzby, Aldos C. Barefoot, III, Michael W. Grayston, Evan D. Laganis, Roy F. Waldron, David M. Lemal

50 Preparation of Fluoroolefins
Moritz F. Kühnel, Dieter Lentz

51 Preparation of Ionic Liquids of Fluorocomplex and Oxofluorocomplex Anions by Fluoroacid-base Reactions
Kazuhiko Matsumoto, Rika Hagiwara

52 Synthesis of Difluorocyclopropyl Building Blocks: 2,2-Difluorocyclopropylmethanol and 2-(Bromomethyl)-1,1-Difluorocyclopropane
Wei Xu, William R. Dolbier, Jr.

53 Preparation of 1,1,2,2,9,9,10,10-Octafluoro[2.2]paracyclophane and Perfluoro[2.2]paracyclophane
William R. Dolbier, Jr., Jian-Xi Duan, Alex J. Roche, Lianhao Zhang

54 Efficient Preparation of Bioorganic Fluorine Compounds
Xiao-Long Qiu

55 1,3-Dipolar Cycloaddition Reactions to Fluoroalkenes
Hanna Wójtowicz-Rajchel, Henryk Koroniak

56 Synthesis of Fluorinated Vinyl Derivatives of Nucleic Acid Bases
Hanna Wójtowicz-Rajchel, Donata Pluskota-Karwatka, Henryk Koroniak

57 Synthesis of CF3-substituted Aziridine Ring by the Gabriel Reaction
Tomasz Cytlak, Bartosz Marciniak, Henryk Koroniak

58 Preparation of α-Fluoro Amino and α-Fluoro Enamino Reagents
Henryk Koroniak, Justyna Walkowiak

59 Synthesis of Original Fluoromonomers and Their Radical copolymerization with Vinylidene fluoride
Bruno Ameduri

60 Convergent 18F Radiosynthesis
V. Gouverneur, O. Lozano

61 Asymmetric Fluorocyclization Reactions
V. Gouverneur. O. Lozano

62 Preparation of Allylic Fluorides
V. Gouverneur, O. Lozano

63 Dehydroxyfluorinations of Primary or Secondary Alcohols Using Perfluoro n-butylsulfonyl Fluoride (nonaflyl Fluoride, NfF) in Combination with 1,8-Diaza-bicyclo[5.4.0]undec-7-ene (DBU)
Orlin Petrov, Matthias Schneider, Rolf Bohlmann, Stephan Vettel, Helmut Vorbrüggen

64 Preparation of Rare Earth Fluorosulfides and Oxyfluorosulfides
A. Demourgues, A.Tressaud

65 Preparation of Carbon-Fluorine Compounds and Fluoride or Oxide Fluoride-Intercalated Graphites
Tsuyoshi Nakajima

66 Safe Synthesis of Superstoichiometric Mesoporous Fluorocarbons
Valentin N. Mitkin

67 Preparation of Fluorinated ?-Alumina
Erhard Kemnitz, Toma? Skapin, John M. Winfield

Index