Handbook of reagents for organic synthesis: fluorine-containing reagents / ed. by Paquette L.A. - Chichester: Wiley, 2007. - 712 p. - ISBN 978-0-470-01177-4  Место хранения:   032 | Институт органической химии им. Н.Н.Ворожцова СО РАН | Новосибирск | Библиотека

Оглавление / Contents

Preface ...................................................... xiii Introduction ................................................... xv Recent Monographs and Overview Articles ......................... 1 Organic Syntheses Procedures Featuring the Preparation of Organofluorine End-Products and of Fluorinated Reagents as Promoters, Volumes 68-82 ............................ 3 Acetyl Hypofluorite ............................................. 9 Allylpentafluorobenzene ........................................ 10 Aluminum(III) Fluoride ......................................... 13 Antimony(V) Fluoride ........................................... 16 Arsenic(III) Fluoride .......................................... 21 Benzoyl Trifluoromethanesulfonate .............................. 23 N-Benzyltriflamide ............................................. 24 Bismuth Pentafluoride .......................................... 26 Bis(pentafluorophenyl)carbonate ................................ 28 Bis(2,2,2-trifiuoroethyl) Chlorophosphate ...................... 29 Bis(2,2,2-trifluoroethyl)malonate .............................. 35 3,5-Bis(trifluoromethyl)acetophenone ........................... 36 Bis(trifluoromethyl)cadmium .................................... 41 2,2-Bis(trifluoromethyl)-2-hydroxyacetic Acid (BTHA) ........... 43 Bis(trifluoromethyl)mercury .................................... 44 3,5-Bis(trifluoromethyl)thiophenol ............................. 46 Boron Trifluoride-Acetic Anhydride ............................. 50 Boron Trifluoride Etherate ..................................... 55 Boron Trifluoride .............................................. 71 Bromine Trifluoride ............................................ 75 2-Bromo-3,3,3-trifiuoropropene.................................. 81 Bromochlorodifluoromethane ..................................... 83 3-Bromo-3,3-difluoropropene .................................... 86 2-Bromofiuorobenzene ........................................... 90 Bromotrifluoroethylene ......................................... 91 Bromotrifluoromethane .......................................... 93 Bromodifluorophenylsulfanylmethane ............................. 99 N-{t-Buty ldimethylsily O-N-methy ltrifiuoroacetamide ......... 101 Cerium(IV) Trifluoroacetate ................................... 103 Cesium Fluoride ............................................... 103 Chlorodifluoromethane ......................................... 117 l-Chloro-2,3,4,5,6-pentafluorobenzene (CPFB) .................. 118 l-Chloro-2,2,2-trifluoroethane (HCFC-133a) .................... 123 (2-Chloro-1,1,2-trifluoroethy l)-diethy lamine ................ 127 Chlorotrifluoroethylene ....................................... 128 Copper(I) Fluoride and Copper(II)Fluoride ..................... 129 Copper(I) Trifluoromethanesulfonate ........................... 133 Copper(II) Trifluoromethanesulfonate .......................... 156 Crotyltrifluorosilane ......................................... 163 Cyanuric Fluoride ............................................. 164 Dibromodifluoromethane ........................................ 167 1,2-Dibromo-1,1,2,2-tetrafluoroethane ......................... 173 Di-t-butylsilyl Bis(trifluoromethanesulfonate) ................ 175 Dichlorofluoromethane ......................................... 176 N,N-Diethylaminosulfur Trifluoride ............................ 180 N,N-Diethyl-2-chloro-1,1,2-trifluoroethylamine ................ 194 Diethyl Fluoromalonate ........................................ 195 Diethyl( 1,1,2,3,3,3-hexafluoropropyl)amine ................... 197 Difluoramine .................................................. 200 1,3-Difluorobenzene ........................................... 201 2,3 -Difluoro-p-benzoquinone .................................. 203 2,6-Difluoro-p-benzoquinone ................................... 204 Difluoromaleic Acid ........................................... 204 Difluoromaleic Anhydride ...................................... 206 (Difluoromethylene)cyclopropane ............................... 207 Difluoromethylenetriphenylphosphorane ......................... 209 Difluoromethyl Phenyl Sulfone ................................. 210 2,6-Difluoropyridine .......................................... 212 2-2-Difluorovinyl-p-toluenesulfonate .......................... 213 Dimethyl Sulfoxide-Trifluoroacetic Anhydride .................. 214 Diphenylbis(1,1,1,3,3,3-hexafluoro-2-phenyl-2-propoxy) sulfurane ..................................................... 215 Diphenyldifluorosilane ........................................ 217 (R,R)-1,2-Diphenyl-1,2-[di(pentafluorophenyl) phosphanoxy]ethane ............................................ 218 DiphenylseleniumBis(trifluoroacetate) ......................... 219 Dirhodium(II) Tetrakis(perfluorobutyrate) ..................... 221 Dirhodium(II) Tetrakis(trifluoroacetate) ...................... 223 EthoxycarbonylmethylTrifluoromethanesulfonate ................. 227 1-Ethoxy-3-trifluoromethyl-1,3-butadiene ...................... 228 Ethyl Bromodifluoroacetate .................................... 229 Ethyl Difluoroiodoacetate ..................................... 233 Ethyl Fluoroiodoacetate ....................................... 234 Ethyl 4,4,4-trifluorocrotonate ................................ 235 Ethyl Trifluoropyravate ....................................... 237 9-Fluorenylmethyl Pentafluorophenyl Carbonate ................. 241 Fluorine ...................................................... 243 2-Fluoroaniline ............................................... 247 N-Fluoro-N-t-butyl-p-toluenesulfonamide ....................... 249 Fluorodimethoxyborane Diethyl Etherate ........................ 251 1-Fluoro-2,4-dinitrobenzene ................................... 252 Fluoroform .................................................... 254 2-Fluoro-4-iodopyridine ....................................... 256 Fluoroketene .................................................. 258 Fluoromethylenetriphenylphosphorane ........................... 260 Fluoromethyl Phenyl Sulfide ................................... 260 Fluoromethyl Phenyl Sulfone ................................... 261 Fluoromethyl Phenyl Sulfoxide ................................. 263 2-Fluorophenol ................................................ 265 2-Fluorophenylboronic Acid .................................... 267 (S)-2-[(R)-Fluoro(phenyl)methyl]oxirane ....................... 268 N-Fluoro-N-(phenylsulfonyl)benzenesulfonamide ................. 270 2-Fluoropyrazine .............................................. 271 2-Fluoropyridine .............................................. 273 3-Fluoropyridine .............................................. 277 N-Fluoropyridinium Triflate ................................... 278 3-Fluoroquinoline ............................................. 279 α-Fluorostyrene ............................................... 280 Fluorosulfuric Acid ........................................... 283 Fluorotributyl(methyl)phosphorane ............................. 286 Fluorotrimethylsilane ......................................... 287 (+/-)-Halothane(2-Bromo-2-chloro-1,1,1-trifluoroethane) ....... 288 Heneicosafluoro-n-decyl Iodide ................................ 289 2,2',4,4',6,6'-Hexafluorobiphenyl ............................. 292 Hexafluoro-tert-butanol ....................................... 293 Hexafluoro-2-butyne ........................................... 295 1,1,1,3,3,3-Hexafluoroisopropyl Acrylate (HFIPA) .............. 304 1,1,1,5,5,5-Hexafluoro-2,4-Pentanedione ....................... 307 Hexafluoropentanedioyl Chloride ............................... 309 1,1,1,3,3,3-Hexafluoro-2-phenyl-2-propanol .................... 312 Hexafluoropropene Oxide (HFPO) ................................ 313 2H-Hexafluoropropyl Azide ..................................... 324 Hydrofluoric Acid ............................................. 325 Hydrogen Fluoride ............................................. 329 2-Hydroperoxyhexafluoro-2-propanol ............................ 333 Hypofluorous Acid ............................................. 334 Iodine Monofluoride ........................................... 336 Iodine Pentafluoride .......................................... 337 Iodine Tris(trifluoroacetate) ................................. 338 Lithium Fluoride .............................................. 340 Lithium Tetra(pentafluorophenyl)borate ........................ 341 Manganese Trifluoride ......................................... 345 Mercury(II) Fluoride .......................................... 348 Mercury(II) Trifluoroacetate .................................. 349 (S)α-Methoxy-α-(trifluoromethyl)phenylacetic Acid ............. 352 Methyl Bis(2,2,2-trifluoroethoxy)phosphinylacetate ............ 355 Methyl Bis(2,2,2-trifluoroethyl)bromophosphonoacetate ......... 356 Methyl Dichlorofluoroacetate .................................. 357 Methyl Difluoroacetate ........................................ 358 Methyl Difluoroiodoacetate .................................... 361 Methyl Fluoride-Antimony(V) Fluoride .......................... 362 Methyl Hypofluorite ........................................... 364 Methyl(trifluoromethyl)dioxirane .............................. 365 Methyl 3,3,3-Trifluoropyruvate ................................ 371 Molybdenum(VI) Fluoride ....................................... 383 Monofluoromethylenediphosphonate .............................. 384 Nonafluorobutanesulfonyl Fluoride ............................. 387 l,l,l,2,2,3,3,4,4-Nonafluoro-6-(methanesulfinyl)hexane ........ 388 Pentafluorobenzoic Acid ....................................... 390 Pentafluorophenol ............................................. 392 Pentafluorophenylboronic Acid ................................. 396 Pentafluorophenylhydrazine .................................... 399 Pentafluoropyridine ........................................... 401 Pentafluorosulfanyl Chloride .................................. 406 Perchloryl Fluoride ........................................... 408 1H,1H,2H,2H-Perfluorodecanethiol .............................. 411 1H,1H,2H,2H-Perfluorooctyl 1,3-dimethylbutyl Ether ............ 413 Perfluoro-N-fluoropiperidine .................................. 415 Phenylsulfonylfluoromethylphosphonate ......................... 416 N-Phenyltrifluoromethanesulfonimide ........................... 417 Potassium Fluoride ............................................ 419 Potassium Hydrogen Fluoride ................................... 422 Potassium Methyltrifluoroborate ............................... 425 Potassium Phenyltrifluoroborate ............................... 427 Potassium Trifluoro-2-propenylborate .......................... 432 Silver(I) Fluoride ............................................ 436 Silver(II) Fluoride ........................................... 438 Silver(I) Heptafluorobutanoate ................................ 441 Silver(I) Trifluoromethanesulfonate ........................... 442 Sodium Chlorodifluoroacetate .................................. 452 Sodium Dichlorofluoroacetate .................................. 454 Sodium Fluoride ............................................... 455 Sulfur Tetrafluoride .......................................... 456 Tetra-n-butylammonium Fluoride ................................ 459 Tetrafluoro-p-benzoquinone .................................... 468 Tetrafluoroboric Acid ......................................... 474 3,3,4,4-Tetrafluoro-4-bromo-l-butene and 3,3,4,4-tetrafluoro-4-iodo-1-butene ........................... 477 Tetrafluorocyclopropene ....................................... 479 1,1,1,2-Tetrafluoroethane ..................................... 483 Tetrafluorophthalic Anhydride ................................. 485 Thallium(III) Trifluoroacetate ................................ 489 Tin(II) Fluoride .............................................. 493 Titanium(IV) fluoride ......................................... 495 Tri-n-butylfluorostannane ..................................... 498 Tri-n-butyltin Trifluoromethanesulfonate ...................... 499 Tributyl(3,3,3-trifluoro-1-propynyl)stannane .................. 500 Trichlorofluoromethane ........................................ 502 Triethoxyfluorosilane ......................................... 505 Triethylamine Trihydrofluoride ................................ 506 Triethyl 2-fluoro-2-phosphonoacetate .......................... 509 Trifluoroacetic Acid .......................................... 511 Trifluoroacetic Anhydride ..................................... 516 Ethyl 4,4,4-trifluoroacetoacetate ............................. 520 Trifluoroacetyl Chloride ...................................... 525 N-Trifluoroacetylimidazole .................................... 525 1,2,3-Trifluorobenzene ........................................ 526 1,3,5-Trifluorobenzene ........................................ 527 4,4,4-Trifluorobutan-2-one .................................... 530 1,1,2-Trifluoroethenyl Zinc (Chloride, Bromide, Iodide) .............................................. 531 2,2,2-Trifluoroethyl Diphenylphosphine Oxide .................. 533 2,2,2-Trifluoroethyl p-Toluenesulfonate ....................... 534 2,2,2-Trifluoroethyl Trifluoroacetate ......................... 536 Trifluoroiodomethane .......................................... 536 Trifluoromethanesulfonic Acid ................................. 537 Trifluoromethanesulfonic Anhydride ............................ 545 Trifluoromethanesulfonyl Chloride ............................. 559 Trifluoromethanesulfonylmethyl Methyl Sulfone ................. 563 o-Trifluoromethylacetophenone ................................. 565 m-Trifluoromethylacetophenone ................................. 567 p-Trifluoromethylacetophenone ................................. 574 ortho-Trifluoromethylbenzaldehyde ............................. 577 meta-Trifluoromethylbenzaldehyde .............................. 581 para-Trifluoromethylbenzaldehyde .............................. 586 m-Trifluoromethylbenzoyl Chloride ............................. 593 Trifluoromethylcopper(I) ...................................... 595 Trifluoromethyl Hypofluorite .................................. 597 (E)-Trifluoromethyl-1-nitroethylene ........................... 601 Trifluoromethyloxirane ........................................ 602 2-(Trifluoromethyl)pyridine ................................... 607 3-(Trifluoromethyl)pyridine ................................... 608 4-(Trifluoromethyl)pyridine ................................... 610 Trifluoromethyl Phenyl Sulfone ................................ 611 {[(Trifluoromethyl) sulfonyl] ethynyl} benzene ................ 613 (5)-N-(Trifluoromethylsulfonyl)-2-isopropylaziridine .......... 615 Trifluoromethylthiocopper(I) .................................. 617 Trifluoromethyltrimethylsilane ................................ 618 Trifluoroperacetic Acid ....................................... 619 l-(3,3,3-Trifluoroprop-1-ynyl)benzene ......................... 624 1,2,2-Trifluorostyrene (TFS) .................................. 627 α,α,α-Trifluorotoluene ........................................ 632 Trifluorovinyllithium ......................................... 635 Trimethylsilyl Fluorosulfonyldifluoroacetate .................. 637 Trimethyl(trifluoromethyl)stannane ............................ 639 Tris(pentafluorophenyl)borane ................................. 640 Tris(2-perfluorohexylethyl)tin Hydride ........................ 645 Tris(trifluoromethyl)difluorophosphine ........................ 648 Vanadyl Trifluoride ........................................... 650 Vinyl(pentafluorocyclopropane) ................................ 651 Xenon(II) Fluoride ............................................ 654 List of Contributors .......................................... 657 Reagent Formula Index ......................................... 671 Subject Index ................................................. 677