Sulfur–Containing Reagents

Professor Leo A. Paquette, Department of Chemistry, Ohio State University, Columbus, OH, USA. Distinguished University Professor; editor and author of a wide list of Wiley publications.

Preface xiii Introduction xv Short Note on InChIs and InChIKeys xvi Organic Syntheses Procedures Featuring the Synthesis of Organosulfur Compounds and Preparative Applications thereof, Volumes 65--85 1 Allyl Triflone 15 Aminoiminomethanesulfonic Acid 16 p-Anisolesulfonyl Chloride 18 Anthracenesulfonamide 19 1-Benzenesulfinyl Piperidine 21 Benzenesulfonic Acid, 2-Nitro-,(1-Methylethylidene) hydrazide 23 Benzenesulfonic Anhydride 25 Benzenesulfonyl Bromide 26 Benzimidazolium Triflate 27 (1R,5R)-2H-1,5-Benzodithiepin-3(4H)-one 1,5-Dioxide 29 3H-1,2-Benzodithiol-3-one 1,1-Dioxide 31 Benzothianthrene Oxide 34 Benzothiazole-2-sulfonyl Chloride 36 4-Benzyloxazolidine-2-thione 37 3-(2-Benzyloxyacetyl)thiazolidine-2-thione 40 Benzyltriethylammonium Tetrathiomolybdate 42 N-Benzyl Triflamide 46 4,4--Bis(2-amino-6-methylpyrimidyl) Disulfide 48 Bis(2,2--bipyridyl)silver(II) Peroxydisulfate 49 N,N--Bis(tert-butoxycarbonyl)-N--- trifluoromethanesulfonylguanidine 50 [N,N--[1,2-Bis(3,5-dimethylphenyl)-1,2-ethanediyl]bis (1,1,1-trifluoromethanesulfonamidato)]methylaluminum 51 2,4-Bis(4-methoxyphenyl)-1,3,2,4-dithiadiphosphetane 2,4-Disulfide 52 2,3-Bis[(4-methylphenyl)thio]-1,3,2,4-dithiadiphosphetane 2,4-Disulfide 68 2,4-Bis(methylthio)-1,3,2,4-dithiadiphosphetane 2,4-Disulfide 69 N-[Bis(methylthio)methylene]-p-toluenesulfonamide 71 Bis[N-(p-toluenesulfonyl)]selenodiimide 80 1-[Bis(trifluoromethanesulfonyl)methyl]-2,3,4,5,6- pentafluorobenzene 81 Bis(4-trimethylsilylphenyl) Disulfide and Bis(4-trimethylsilylphenyl) Diselenide 85 Boron Trifluoride--Dimethyl Sulfide 86 4-Bromobenzenesulfonyl Azide 89 4-Bromobenzenesulfonyl Chloride 90 (4R,5R)-2-Bromo-1,3-bis-(4-methylphenyl sulfonyl)-4,5-diphenyl-1,3,2-diazaborolidine and (4S,5S)-2-Bromo-1,3-bis-(4-methylphenyl sulfonyl)-4,5-diphenyl-1,3,2-diazaborolidine 91 Bromodifluorophenylsulfanylmethane 98 Bromomethanesulfonyl Phenyl Tetrazole (Chloro) 100 2-(2-Butenylthio)benzothiazole 102 tert-Butyl N-Lithio-N-(p-toluenesulfonyloxy)carbamate 103 2-[N-(tert-Butyloxycarbonyl)aminophenyl]ethanethiol 104 tert-Butylsulfonyl Chloride 107 tert-Butyltetrazolylthiol 109 10-Camphorsulfonyl Chloride 111 Carbomethoxysulfenyl Chloride 118 Carbon Disulfide 124 Cerium(IV) Ammonium Sulfate 128 Cesium Fluoroxysulfate 130 N-Chloro-N-cyclohexylbenzenesulfonamide 131 Chloromethyl p-Tolyl Sulfide 132 Chloromethyl p-Tolyl Sulfone 134 4-Chlorophenyl Chlorothionoformate 136 4-(4-Chlorophenyl)-3-hydroxy-2(3H)thiazolethione 137 N-Chlorosuccinimide--Dimethyl Sulfide 140 Chloro(thexyl)borane--Dimethyl Sulfide 144 Copper(II) Sulfate 145 Copper, (2-Thiophenecarboxylato-kappaO2,kappaS1) 152 Copper(II) Toluenesulfonate 157 Copper(I) Trifluoromethanesulfonate 158 Copper(II) Trifluoromethanesulfonate 181 Dibromoborane--Dimethyl Sulfide 189 Dibutyl(trifluoromethanesulfoxy)stannane 197 Dicarbonyl(cyclopentadienyl)[(dimethylsulfonium) methyl]iron Tetrafluoroborate 198 Dichloroborane--Dimethyl Sulfide 200 2-2-Difluorovinyl p-Toluenesulfonate 205 2,5-Dihydro-2,2-dimethyl-5,5-bis(propylthio)- 1,3,4-oxadiazole 206 2,3-Dihydro-2-phenylimidazo[2,1-b]benzothiazole 207 Diisopropyl Methylsulfanyldifluoromethylphosphonate 209 4-(Dimethylamino)pyridinium Chlorosulfite Chloride 211 Dimethyl Bis(methylthio)methylphosphonate 212 6,6-Dimethyl-1,4-diseleno-3,7-tetrasulfide 213 N,N-Dimethyldithiocarbamoylacetonitrile 214 N-(1,1-Dimethylethyl)benzenesulfenamide 215 N,N-Dimethyl-O-(methylsulfonyl)hydroxylamine 217 Dimethyl(methylthio)sulfonium Tetrafluoroborate 219 Dimethyl(methylthio)sulfonium Trifluoromethanesulfonate 225 cis-3-[N-(3,5-Dimethylphenyl)benzenesulfonamido] borneol 230 Dimethylsuccinimidosulfonium Tetrafluoroborate 231 Dimethyl Sulfoxide--Iodine 233 Dimethyl Sulfoxide--Methanesulfonic Anhydride 234 Dimethyl Sulfoxide--Phosphorus Pentoxide 234 Dimethyl Sulfoxide--Silver Tetrafluoroborate 235 Dimethyl Sulfoxide--Sulfur Trioxide/Pyridine 237 S,S-Dimethyl-N-(p-toluenesulfonyl)sulfilimine 238 S,S-Dimethyl-N-(p-toluenesulfonyl)sulfoximine 239 2,4-Dinitrobenzenesulfonyl Chloride 240 3,5-Dinitrobenzenesulfonyl Chloride 242 2,4-Dinitrobenzenesulfonylhydrazide 243 2-(1,3-Dioxan-2-yl)ethylsulfonyl Chloride 244 1,1-Dioxobenzo[b]-thiophene-2-yl Methyloxycarbonyl Chloride 246 Diphenylbis(1,1,1,3,3,3-hexafluoro-2-phenyl-2- propoxy)sulfurane 246 (R,R)-1,2-Diphenyl-1,2-diaminoethane N,N--Bis[3,5-bis(trifluoromethyl)benzenesulfonamide] 248 N-(Diphenylmethylene)benzenesulfonamide and N-(Diphenylmethylene)-4-methylbenzenesulfonamide 250 Diphenyl Sulfoxide 253 2,2--Dipyridyl Disulfide-N,N--dioxide 258 1,2,4-Dithiazolidine-3,5-dione 262 1,3-Dithienium Tetrafluoroborate 266 trans-1,3-Dithiolane 1,3-Dioxide 267 1,4-Dithiothreitol 268 tert-Dodecanethiol 269 p-Dodecylbenzenesulfonyl Azide 272 Ethyl (Dimethylsulfuranylidene)acetate 275 S-Ethyl Ethanethiosulfinate 279 4-Ethylhexahydro-4-methyl-(4S,9aS)- pyrrolo[1,2-d][1,4]thiazepin-5(4H)-one 282 5-Ethylthio-1H-tetrazole 283 2-Fluoro-3,3-dimethyl-2,3-dihydro-1,2-benzisothiazole 1,1-Dioxide 287 N-Fluoro-N-(phenylsulfonyl)benzenesulfonamide 288 Fluorosulfuric Acid 291 Fluorosulfuric Acid--Antimony(V) Fluoride 294 Glyoxylyl Chloride p-Toluenesulfonylhydrazone 299 2-Hydroxyethyl Phenyl Sulfone 305 [Hydroxy(tosyloxy)iodo]benzene 307 Isopropyldiphenylsulfonium Tetrafluoroborate 317 (S)-4-Isopropylthiazolidine-2-thione 318 (1R,2S)-1-Lithio-1-phenylsulfonyl-2- [(tert-butyldiphenyl)silyl]oxymethyloxirane 321 2-Lithio-N-phenylsulfonylindole 323 Lithium Butyl(phenylthio)cuprate 325 Lithium Cyclopropyl(phenylthio)cuprate 326 Lithium (3,3-Diethoxy-1-propen-2-yl)(phenylthio)cuprate 327 Lithium 2-Lithiobenzenethiolate 329 Lithium 1-Methyl-2-(2-methyl-1-(E)-propenyl)- cyclopropyl(phenylthio)cuprate 330 Lithium Phenylthio(trimethylstannyl)cuprate 333 Lithium Phenylthio(2-vinylcyclopropyl)cuprate 334 (-)-(1R,2S,5R)-Menthyl (S)-p-Toluenesulfinate 337 6-Mercapto-4-dibenzofuranol 340 1-(Mesitylene-2-sulfonyl)-3-nitro-1,2,4-triazole (MSNT) 342 Mesitylsulfonyl-1H-1,2,4-triazole 345 (R,R)-1,2-(Methanesulfonamido)-cyclohexane 346 Methanesulfonic Anhydride 349 Methanesulfonyl Chloride--Dimethylaminopyridine 350 Methoxycarbonylmethanesulfonyl Chloride 351 Methoxycarbonylsulfamoyl Chloride 351 4-Methoxycarbonylthiolan-3-one 352 2-(2-Methoxyethoxy)-ethyl 2-(Chlorosulfonyl)-benzoate 354 Methoxyphenyl Benzenethiosulfinate 357 1-(4-Methoxyphenyl)-2-(4--methylbenzylthio)ethylamine 358 7-Methoxy-3-(phenylsulfonyl)-1(3H)-isobenzofuranone 361 Methoxy(phenylthio)methane 362 Methoxy(phenylthio)trimethylsilylmethane 364 2-Methylallyl Phenyl Sulfone 366 2-Methylbenzothiazole 369 Methylbis(methylthio)sulfonium Hexachloroantimonate 371 Methyl alpha-Chloro-alpha-phenylthioacetate 373 Methyl Diethylamidosulfite 374 Methyl Methanethiosulfonate 374 4-Methyl-N-phenylbenzene Sulfonimidoyl Chloride 377 1-Methyl-2(1H)-pyridinethione 380 Methylsulfenyl Trifluoromethanesulfonate 380 (+)-(S)-N-Methylsulfonylphenylalanyl Chloride 381 2-Methylsulfonyl-3-phenyl-1-prop-2-enyl Chloroformate 382 Methyl Thioglycolate 384 Methylthiomaleic Anhydride 385 1-(Methylthiomethyl)benzotriazole 386 Methylthiomethyl p-Tolyl Sulfone 387 (E)-3-Methylthio-2-propenyl p-Tolyl Sulfone 390 2-(Methylthio)tetrahydrofuran 391 5-Methylthio-1H-tetrazole 391 Methyl N-(p-Toluenesulfonyl)carbamate 392 alpha-Methyltoluene-2,alpha-sultam 395 Methyl p-Toluenethiosulfonate 397 N-Methyltrifluoromethanesulfonamide 398 Methyltrifluoromethanesulfonate 399 (-)-2-exo-Morpholinoisobornane-10-thiol 408 o-Nitrobenzenesulfonyl Azide 411 o-Nitrobenzenesulfonyl Chloride 412 o-Nitrobenzenesulfonylhydrazide 415 p-Nitrobenzenesulfonyl-4-nitroimidazole 417 p-Nitrobenzenesulfonyloxyurethane 418 5-Nitro-3H-1,2-benzoxathiole S,S-Dioxide 419 Nitrosylsulfuric Acid 420 1,1,1,2,2,3,3,4,4-Nonafluoro-6-(methanesulfinyl)hexane 422 Oxodimethoxyphosphoranesulfenyl Chloride 425 Pentafluorosulfanyl Chloride 427 1H,1H,2H,2H-Perfluorodecanethiol 428 Peroxydisulfuryl Difluoride 430 Phenyl Chlorothionocarbonate 432 1-Phenyl-2-(phenylsulfanyl)ethyl Acetate 434 4-Phenylsulfonyl-2-butanone Ethylene Acetal 436 N-(Phenylsulfonyl)(3,3-dichlorocamphoryl)oxaziridine 437 (2-Phenylsulfonyl)ethoxy Dichlorophosphine 439 alpha-Phenylsulfonylethyllithium 440 (2-Phenylsulfonylethyl)trimethylsilane 444 Phenylsulfonylfluoromethylphosphonate 445 (1S,6S)-2-(Phenylsulfonyl)-7-oxabicyclo[4.1.0]hept-2-ene 446 (E,E)-N-Phenylsulfonyl-4-phenyl-1-aza-1,3-butadiene 449 3-(Phenylsulfonyl)propanal Ethylene Acetal 451 1-Phenylsulfonyl-1H-tetrazole 452 (E)-1-Phenylsulfonyl-2-trimethylsilylethylene 453 1-Phenyl-2-tetrazoline-5-thione 454 2-Phenylthioethanol 456 (Phenylthio)nitromethane 457 N-Phenylthiophthalimide 459 1-Phenylthiovinyl Triphenylphosphonium Iodide 460 Se-Phenyl p-Tolueneselenosulfonate 461 N-Phenyltrifluoromethanesulfonimide 465 Phthalimidosulfenyl Chloride 469 Potassium tert-Butoxide--Dimethyl Sulfoxide 471 Potassium Hydroxide--Dimethyl Sulfoxide 474 Potassium Monoperoxysulfate 475 Potassium o-Nitrobenzeneperoxysulfonate 487 Potassium Nitrosodisulfonate 489 1,3-Propanedithiol Bis(p-toluenesulfonate) 491 N-Propenoyl Camphor-10,2-sultam 493 3-Propionylthiazolidine-2-thione 495 2-Pyridinesulfonyl Chloride 496 N-(2-Pyridyl)bis(trifluoromethanesulfonimide) 498 Sodium Dodecyl Sulfate 501 N-Sulfinyl-p-toluenesulfonamide 503 9-(2-Sulfo)fluorenylmethoxycarbonyl Chloride 505 Sulfonic Acid, Polymer-supported 506 o-Sulfoperbenzoic Acid 515 Sulfur Trioxide 516 N,N,N-,N--Tetrabromobenzene-1,3-disulfonamide (TBBDS) 521 Tetrachlorothiophene Dioxide 523 2,2,4,4-Tetramethylcyclobutan-1-one-3-thione 527 1,1--(Thiocarbonyl)bis(1H-benzotriazole) 533 2-Thiono-1,3-dioxol-4-ene 535 Thiophenol--Azobisisobutyronitrile 535 Thiophenol, Polymer-supported 536 Thiophosphoryl Chloride 537 2-Thiopyridyl Chloroformate 538 Thiourea Dioxide 540 p-Toluenesulfinic Acid 541 p-Toluenesulfonyl Bromide 542 p-Toluenesulfonyl Chloride and Related Reagents, Polymer-supported 545 O-p-Toluenesulfonylhydroxylamine 548 [N-(p-Toluenesulfonyl)imino]phenyliodinane 550 p-Toluenesulfonylmethylene Triphenylphosphorane 553 (R)-(+)-p-Tolylsulfinylacetic Acid 555 (R)-(+)-alpha-(p-Tolylsulfinyl)-N,N-dimethylacetamide 556 R)-(+)-3-(p-Tolylsulfinyl)propionic Acid 557 Tosyl Azide, Polymer-supported 558 beta-Tosylethylamine 559 beta-Tosylethylazide 560 6-Tosyl-3-oxa-6-azabicyclo[3.1.0]hexane 561 Tri(tert-butoxy)silanethiol 563 Tricarbonyl[(2,3,4,5,6,7-eta)-thiepin-1,1- dioxide]chromium(0) 566 2,2,2-Trichloroethoxysulfonamide 568 2,2,2-Trichloroethyl-N-tosyloxycarbamate 571 Triethylsilyl Trifluoromethanesulfonate 572 Trifluoromethanesulfonic Acid 573 Trifluoromethanesulfonic Anhydride 581 Trifluoromethanesulfonyl Azide 595 Trifluoromethanesulfonyl Chloride 598 Trifluoromethanesulfonylmethyl Methyl Sulfone 602 S-(Trifluoromethyl)dibenzothiophenium Triflate 603 Trifluoromethyl Phenyl Sulfone 604 {[(Trifluoromethyl)sulfonyl]ethynyl}benzene 606 (S)-N-Trifluoromethylsulfonyl-2-isopropylaziridine 607 [1,1,1-Trifluoro-N- [(trifluoromethyl)sulfonyl]methanesulfonamidato- kappaN](triphenylphosphine) 610 1,1,1-Trifluoro-N-[(trifluoromethyl)sulfonyl]-N- (trimethylsilyl)methanesulfonamide 613 2,4,6-Triisopropylbenzenesulfonyl Azide 616 2,4,6-Triisopropylbenzenesulfonyl Hydrazide 623 Triisopropylbenzenesulfonyl Tetrazole 629 Triisopropylsilylethynyl Triflone 632 Triisopropylsilyl Trifluoromethanesulfonate 633 2-Trimethylsilyl-1,3-benzothiazole 635 [N-(2-(Trimethylsilyl)ethanesulfonyl)imino]phenyliodane 636 (Trimethylsilyl)methanesulfonyl Chloride--Cesium Fluoride 638 2-(Trimethylsilyl)phenyl Triflate 639 Triphenylphosphonium 3,3-Dimethyl-1,2,5- thiadiazolidine 1,1-Dioxide 642 Triphenyl Thioborate 644 Trityl Thionitrite 645 List of Contributors 647 Reagent Formula Index 663 Subject Index 669