Wiley
Wiley.com
Print this page Share
E-book

Handbook of Reagents for Organic Synthesis, Sulfur-Containing Reagents

Leo A. Paquette (Editor)
ISBN: 978-1-118-63486-8
736 pages
May 2013, Wiley-Blackwell
Handbook of Reagents for Organic Synthesis, Sulfur-Containing Reagents (1118634861) cover image
There are a lot of books available about the chemistry and biology of sulfur. However, this is the first book with a compilation of all relevant Sulfur containing reagents. Synthetic chemists, most particularly in the medicinal and pharmaceutical chemists, are often called upon to prepare compounds that contain Sulfur as a key structural feature. In the past, this seemed to be a domain for specialists; today every synthetic chemist working in these area is expected to synthesize compounds containing sulfides, sulfates, sulfones, etc. This book offers an important source of information for the selection and handling of the right reagents.
See More

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-κO2,κS1) 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 α-Chloro-α-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

α-Methyltoluene-2,α-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

α-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)-(+)-α-(p-Tolylsulfinyl)-N,N-dimethylacetamide 556
R)-(+)-3-(p-Tolylsulfinyl)propionic Acid 557

Tosyl Azide, Polymer-supported 558

β-Tosylethylamine 559

β-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-η)-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- κN](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

See More

Related Titles

Back to Top