Fluorocarbon and Related Chemistry Vol. 2 A review of the literature published during 1971 and 1972 PDF
Preview Fluorocarbon and Related Chemistry Vol. 2 A review of the literature published during 1971 and 1972
A Specialist Periodical Report Fluorocarbon and Related Chemistry Volume 2 A Review of the Literature Published during 1971 and 1972 Senior Reporters R. E. Banks M.G . Barlow Reporters J. M. Birchall R. Fields W. T. Flowers D. R. Taylor All ot Department of Ch,mistrj Universit of Manch ster Institute of Science and Technology 0 Copyright 1974 The Chemical Society Burlington House, London, W1 V OBN ISBN :0 85186 514 3 Library of Congress Catalog Card No. 72-78530 Printed by Eyre & Spottiswoode Ltd, Thnet Press, Margale Preface This is the second volume in a series of biennial reviews concerned with the chemistry of organic, organometallic, and organometalloidal compounds of the fluorocarbon class and of their polfluorinated analogues. As in the first volume (referred to throughout as Vol. l), compounds containing a low proportion of C-F bonds are mentioned only when relevant to the main theme. The fluorocarbon literature boomed during the two-year period now reviewed, so we have cause to congratulate ourselves on acquiring the sterling services of our friends and colleagues Mike Birchall, Roy Fields, Thain Flowers, and David Taylor as contributing authors. Without their aid and the remarkable skill of our dedicated typist Mrs. Joan Colclough, it would have taken us much longer to produce the typescript. We also greatly appreciate the assistance given by Michael P. Amor, our proof-reader, and David H. Whitehurst, our Departmental Librarian. R.E.B. September 1973 M.G.B. Contents Chapter 1 Saturated Fluorocarbons, FI uorocarb on Hy drides, and Fluorocarbon Halides 1 By R. E. Banks 1 Fluorocarbons 1 2 Hydrides 10 3 Halides 21 4 Bibliography 34 Chapter 2 Per- and Poly-fluorinated Olefins, Dienes, He terocum ulenes, and Acetylenes 37 By M. G. Barlow and D. R. Taylor 1 Olefins 37 Physical Aspects 37 Preparation 43 Ionic Reactions 51 Free-radical React ions 72 Cycloaddit ion Reactions 77 2 Valence-bond Isomers of Aromatic Compounds 84 3 1,SDienes 88 4 Allenes (1,2-Dienes) 94 5 Heterocumulenes (Ketens, Thioketens, etc.) 98 6 Acetylenes 106 7 Bibliography 121 Chapter 3 Aliphatic Per- and Poly-fluorinated Carbonyl and Thiocarbonyl Compounds 12 4 By R. E. Banks 1 Carboxylic Acids and their Derivatives 12 4 Monocarboxylic Acids 124 Dicarboxylic Acids 138 2 Aldehydes 145 3 Ketones 148 4 Bibliography 165 vi Contents Chapter 4 Per- and Poly-fluorinated Aliphatic Derivatives of the Main-group Elements 178 By R. E. Banks 1 Group I 178 Lithium 178 2 Group I1 186 Magnesium 186 Calcium 188 Zinc 188 Cadmium 189 Mercury 189 3 Group 111 195 Boron 195 Aluminium 195 Indium 196 4 Group IV 196 Silicon 196 Germanium 202 Tin 203 5 Group V 204 Nitrogen 204 Amines, Imines, Cyanides, Isocyanides, and Isocyanates 204 Nitroxides, Hydroxylamines, and Nitroso- and Nitro- compounds 223 Azides, Diazoalkanes, Diazirines, Azo- and Hydrazo- compounds, and Azines 235 Phosphorus 244 Arsenic 252 Antimony 252 6 Group VI 252 Oxygen 252 Alcohols, Alkoxides, and Ethers 252 Perfluoroalkyl Hypohalites, Fluoroperoxides, Hydro- peroxides, Peroxides, and Trioxides 262 Sulphur 269 Compounds containing Bivalent Sulphur 269 PerfluoroalkanesulphonicA cids and Related Compounds 276 Derivatives of Sulphur Tetra- and Hexa-fluoride 282 Selenium 284 7 Bibliography 284 Contents vii Chapter 5 Per- and Poly-fluorinated Aliphatic Derivatives of the Transition Elements 290 By R. Fields 1 Introduction 290 2 Groups III-V and the Lanthanides 290 3 Chromium, Molybdenum, and Tungsten 292 4 Manganese and Rhenium 297 5 Iron, Ruthenium, and Osmium 302 6 Cobalt, Rhodium, and Iridium 315 7 Nickel, Palladium, and Platinum 326 8 Copper, Silver, and Gold 344 Chapter 6 Per- and Poly-fluorinated Aromatic Compounds 350 By J. M. Birchall, M. G. Barlow, and W. 1. Flowers 1 Carbocyclic Compounds 350 The Introduction of Fluorine into Aromatic Rings 350 The Introduction of Fluorinated Side-chains 356 Arenes from Aliphatic and Alicyclic Precursors 359 Fluorocarbons, Fluorohydrocarbons, and Polyfluorohalo- geno-compounds 36 1 Olefinic Compounds and Related Polymers 374 Alcohols, Phenols, and Ethers 377 Carbonyl Compounds 380 Carboxylic Acid Derivatives 391 Arynes and Derived Compounds 397 Derivatives of Nitrogen 407 Physical Measurements and Calculations 41 7 2 Derivatives of the Transition Metals 420 Tetrafluorobenzobarrelene 420 Titanium and Hafnium 421 Vanadium 421 Molybdenum and Tungsten 421 Iron and Ruthenium 422 Cobalt, Rhodium, and Iridium 422 Nickel, Palladium, and Platinum 424 Copper and Gold 425 3 Derivatives of the Main-group Elements 427 Lithium 427 Calcium, Magnesium, and Mercury 427 Boron, Thallium, and Indium 429 viii Contents Silicon, Germanium, and Tin 430 Phosphorus, Arsenic, Antimony, and Bismuth 435 Sulphur and Selenium 436 4 Heterocyclic Compounds 439 Introduction of Fluorine 439 Reactions 443 Preparation of Polycyclic Compounds 45 1 Chapter 7 Progress in Nuclear Magnetic Resonance Spectroscopy 456 By M. G. Barlow 1 Introduction 456 2 TemperaturedependentP henomena 458 3 Studies involving 13CN uclei 462 4 Chemically Induced Dynamic Nuclear Spin Polarization of 19F Nuclei 463 5 Through-space Coupling 465 6 Fluoroalkanes 466 7 Solvent Dependence 467 8 Aromatic Compounds 468 Appendix I 470 Appendix II 473 Author Index 475
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