Description

Book Synopsis
Reduction and oxidation processes are at the heart of almost all synthetic procedures and organic chemists are keen to have a huge portfolio of slick and modern catalytic reagents performing oxidations or reductions. This new volume is part of the Handbook for Reagents for Organic Synthesis series, making use of the leading reagent database e-EROS.

Table of Contents

Preface xi

Introduction xiii

Terminal Oxidants Finder xv

Oxidation Catalyst Finder xix

Recent Review Articles and Monographs xxv

Short Note on InChIs and InChIKeys xxvii

4-Acetamido-2,2,6,6-tetramethyl-1-piperidinyloxyl 1

4-Acetylamino-2,2,6,6-tetramethylpiperidine-1-oxoammonium Tetrafluoroborate 2

Bathocuproine 15

Bathophenanthroline 17

Benzenecarboperoxoic acid, 1, 1-dimethylethyl Ester 20

1,2-Benziodoxol-3(1H)-one, 1-Hydroxy, 1-Oxide, IBX 32

1,2-Benziodoxol-3(1H)-one, 1-Hydroxy, 1-Oxide, stabilized (stabilized IBX) 44 1,4-Benzoquinone 49

cis-4-Benzyloxy-α,α-bis-(3,5-dimethylphenyl)-Lprolinol (2S,4R)- 52

2,2_-Bipyrrolidines, (2S,2_S) and (2R,2_R) 54

2-[Bis-[3,5-bis(trifluoromethyl)Phenyl] [(trimethylsilyl)oxy]Methyl]Pyrrolidine 57

2,2-Bis[2-[4(S)-tert-butyl-1,3-oxazolinyl]]propane 59

Bis[[(1R,1__R)-3,3__-[(1R,2R)-1,2-cyclohexanediylbis [(nitrilo-κN)methylidyne]]bis[2_-phenyl[1,1_-
binaphthalen]-2-olato-κO]](2-)]di-μ-oxodi-titanium and Bis[[(1S,1__S)-3,3__-[(1S,2S)-1,2- cyclohexanediylbis[(nitrilo-κN)methylidyne]]bis [2_-phenyl[1,1_-binaphthalen]-2-olato-κO]](2-)]di- μ-oxodi-titanium 66

Bis(2,2-dimethylpropanoato - κ-O)phenyl-iodine 69

Bis(1-methyl-1-phenylethyl) Peroxide 77

1,2-Bis(phenylsulfinyl)ethane 79

N,N_-Bis(2,4,6-trimethylphenyl)imidazol-2-ylidene Palladium(I) Allyl Chloride 82

Bis(trimethylsilyl) Peroxide 87

Bromamine-T 91

N-tert-Butyl-N-chlorocyanamide 94

tert-Butyl Hydroperoxide 96

tert-Butyl Hypochlorite 126

tert-Butyl Peracetate 132

Calcium Hypochlorite 137

Chloramine-T 142

Chlorobenzene 150

Chloro[N,N_-ethylenebis(salicylideneaminato)] manganese 152

Chromium(VI) Oxide 157

Chromyl Acetate 163

Cobalt, [5,10,15,20-tetraphenyl-21H,23Hporphinato( 2−)-κN 21,κN 22,κN 23,κN 24]- 167

Cumyl Hydroperoxide 171

N,N_-(1R,2R)-1,2-Cyclohexanediylbis- [N-hydroxy-α-phenybenzeneacetamide] 179

1,5-Diaza-cis-decalin 183

N,N-Dibromobenzenesulfonamide and N,N-Dibromo-p-toluenesulfonamide 188

Di-μ-chlorobis(1,5-cyclooctadiene)diiridium(I) 195

Di-μ-chlorodichlorobis[(1,2,3,4,5-η)-1,2,-3,4,5- pentamethyl-2,4-cyclopentadien-1-yl]diiridium 202

(R)-2,10-Dichloro-5H-dinaphtho[2,1-g: 1,2-i][1,5]dioxacycloundecin-3,6,9(7h)-trione 210

Dichloro(ethoxy)oxovanadium(V) 213

1,1_-Difluoro-2,2_-bipyridinium Bis-(tetrafluoroborate) 217

1,2:4,5-Di-O-isopropylidene-β-d-erythro-hexo-2,3- diulo-2,6-pyranose 221

Di-μ-methoxobis(1,5-cyclooctadiene)diiridium(I) 224

Dimethyldioxirane 228

(S,S)-2,2_-(Dimethylmethylene)bis(4-tert-butyl-2- oxazoline) and (R,R)-2,2_-(Dimethylmethylene)bis- (4-tert-butyl- 2-oxazoline) 234

Dispiro[2H-pyran-2,4_-[4H-5,6,8b]triazaacenaphthylene- 7_(5_H),2__-[2H]pyran], 1_,2_,2_a,3,3_,3__,4,4__,5,5__,
6,6__,8_,8_a-tetradecahydro-1_,2_-dimethoxy-6,6__- dimethyl-, monohydrochloride, (1_S,2R,2_S,2__R, 2_aS,6S,6__S,8_aS)- 257

N-fluoro-N-(phenylsulfonyl)-benzenesulfonamide 259

N-Fluoropyridinium Tetrafluoroborate 270

N-Fluoropyridinium Triflate 272

1-Fluoro-2,4,6-trimethylpyridinium Tetrafluoroborate 274

1-Fluoro-2,4,6-trimethylpyridinium Trifluoromethanesulfonate 278

Hydrogen Peroxide 281

Hydrogen Peroxide–Urea 295

N-Hydroxyphthalimide 307

Iodine 317

2-Iodobenzenesulfonic Acid 332

Iodosylbenzene 338

Iridium, [N-[(1R,2R)-2-(amino-κN)-cyclohexyl]-4- methylbenzenesulfonamidato-κN]chloro[(1,2,3,4,5-η)-
1,2,3,4,5-pentamethyl-2,4,- cyclopentadien-1-yl]-; Iridium, [N-[(1R,2R)-2-(amino-κN)- cyclohexyl]-4-
methylbenzenesulfonamidato-κN]chloro[(1,2,3,4,5-η)- 1,2,3,4,5-pentamethyl-2,4,-cyclopentadien-1-yl]-; Iridium, [N-[(1S,2S)-2-(amino-κN)cyclohexyl]-4- methylbenzenesulfonamidato-κN]-chloro [(1,2,3,4,5-η)-1,2,3,4,5-pentamethyl-2,4,-
cyclopentadien-1-yl]- 354

Iridium, Dichlorodi-μ-hydrobis[(1,2,3,4,5-η)- 1,2,3,4,5-pentamethyl-2,4-cyclopentadien-1-yl]di- 357

Iron, Bis(pyridine)bis(2-pyridinecarboxylato-N1,O2) 359

Lithium Hydroperoxide 363

Manganese(III) Acetate 367

Manganese(II), bis(octahydro-1,4,7-trimethyl-1H-1,4,7- triazonine-κN1,κN4,κN7)tri-μ-oxodi-, hexafluorophosphate 375

Manganese(II) tetraphenylporphyrin 378

9-Mesityl-10-methylacridinium Perchlorate 381

N-Methylmorpholine N-Oxide 384

(S)-(−)-4-(2-Methylpropyl)-2-(2-pyridyl)-2-oxazoline 388

Methyl(trifluoromethyl)dioxirane 390

Methyltrioxorhenium 396

Molybdenum Chloride Oxide 407

Noyori Oxidation (Sodium Tungstate Dihydrate, Hydrogen Peroxide, Methyltri-n-octylammonium Hydrogen Sulfate, Phosphonic Acid) 411

3,3_,3α,3α _,4,4_,5,5_-Octahydro-3,3,3_,3_-tetraisopropyl- 6,6_-spirobi-[6H-cyclopent[c]isoxazole] 415

4,4,4_,4_,5,5,5_,5_-Octamethyl-2,2_-bi-1,3,2-dioxaborolane 421

Osmium Tetroxide 433

μ-Oxo-bis[tetrakis(t-butyl)-phthalocyaninatoiron(III)] 452

Oxygen 454

Palladium (II) Sparteine Dichloride 467

Peracetic Acid 470

(8α,9R)-(8__ α,9__R)-1,1__-[1,3-Phenylene-bis(methylene)] bis[9-hydroxy-cinchonanium] Dibromide and (9S)-(9__S)-1,1__-[1,3-Phenylene-bis(methylene)] bis[9-hydroxy-cinchonanium]Dibromide 478

(−)(1S)-1-Phenylethyl Hydroperoxide and (+)(1R)-1-Phenylethyl Hydroperoxide 480

(8α,9R)-(8__ α,9__R)-9,9__-[1,4-Phthalazinediylbis(oxy)] bis[10,11-dihydro-6_-methoxycinchonan] & (9S)-(9__S)-9,9__-[1,4-Phthalazinediylbis(oxy)] bis[10,11-dihydro-6_-methoxycinchonan] 483

Picolinic Acid 495

Polyaniline 498

Potassium Bromate 502

Potassium Monoperoxysulfate 506

2-Pyrazinecarboxylic Acid 524

2,3-Pyrazinedicarboxylic Acid 530

Pyrrolidine, 3,4-bis(diphenylphosphino)-1- (phenylmethyl)-,(3R,4R) and Pyrrolidine, 3,4-bis(diphenylphosphino)-1-(phenylmethyl)-, (3S,4S) 532

2-Pyrrolidinemethanol-α,α-bis(3,5-dimethylphenyl)- (2S); and 2-Pyrrolidine-methanol-α,α-bis(3,5- dimethylphenyl)-(2R) 535

Rhenium(VII) Oxide 541

[RuCl2(p-cymene)2]2 546

Ruthenium(III) Chloride 549

Ruthenium Complex of N,N_,N_-Trimethyl-1,4,7-triazacyclononane and Ruthenium Complex of cis-Diaquabis
(6,6_-Dichloro-2,2_-bipyridine) 561

Ruthenium Dodecacarbonyltri Triangulo 565

Ruthenium Hydroxide 568

Selenium(IV) Oxide 575

Sodium Bromate 583

Sodium Hypochlorite 587

Sodium Hypochlorite–N,N_-Bis(3,5-di-tertbutylsalicylidene)- 1,2-cyclohexanediaminomanganese( III) Chloride 600

Spiro[6H-1,3-dioxolo[4,5-c]pyran-6,5_-oxazolidine]-3_- carboxylic acid, tetrahydro-2,2-dimethyl-2_,7- dioxo-,2-methyl-2-propyl ester, (3aR, 5_S, 7aR)- 604

Tetrabutylammonium Bis(pyrazinecarboxylato)- dioxo-vanadium(V) 609

Tetrabutylammonium Dodecatungstophosphate 611

Tetrabutylammonium Peroxydisulfate 615

5,6,7,8-Tetrafluoro-1-hydroxy-1-oxobenziodoxol- 3(1H)one (Tetrafluoro-IBX) 618

2,2,6,6-Tetramethylpiperidin-1-oxyl 620

Tetra-n-propylammonium Perruthenate 626

3,3_,5,5_-Tetra-tert-butyldiphenoquinone 630

(S)-2-(5-1H-Tetrazolyl)pyrrolidine and (R)-2-(5-1H-Tetrazolyl)pyrrolidine 633

4,4_,4__-tri-tert-butyl-2,2_:6_,2__-terpyridine 639

Trichloroisocyanuric Acid 642

Trifluoroperacetic Acid 649

Trimethylamine N-Oxide 659

Triphenylmethyl Hydroperoxide 667

Tris(2-pyridylmethyl)amine 670

Tris[4-(trifluoromethyl)phenyl]phosphine 677

Vanadium,bis[N-[(1S)-1-(carboxy-κO)ethyl]-N- (hydroxy-κO)-l-alaninato(2-)-κN,κO]- 681

Vanadyl Bis(acetylacetonate) 684

List of Contributors 693

Reagent Formula Index 707

Subject Index 711

Handbook of Reagents for Organic Synthesis

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      Publisher: John Wiley & Sons Inc
      Publication Date: 24/09/2013
      ISBN13: 9781119953272, 978-1119953272
      ISBN10: 1119953278

      Description

      Book Synopsis
      Reduction and oxidation processes are at the heart of almost all synthetic procedures and organic chemists are keen to have a huge portfolio of slick and modern catalytic reagents performing oxidations or reductions. This new volume is part of the Handbook for Reagents for Organic Synthesis series, making use of the leading reagent database e-EROS.

      Table of Contents

      Preface xi

      Introduction xiii

      Terminal Oxidants Finder xv

      Oxidation Catalyst Finder xix

      Recent Review Articles and Monographs xxv

      Short Note on InChIs and InChIKeys xxvii

      4-Acetamido-2,2,6,6-tetramethyl-1-piperidinyloxyl 1

      4-Acetylamino-2,2,6,6-tetramethylpiperidine-1-oxoammonium Tetrafluoroborate 2

      Bathocuproine 15

      Bathophenanthroline 17

      Benzenecarboperoxoic acid, 1, 1-dimethylethyl Ester 20

      1,2-Benziodoxol-3(1H)-one, 1-Hydroxy, 1-Oxide, IBX 32

      1,2-Benziodoxol-3(1H)-one, 1-Hydroxy, 1-Oxide, stabilized (stabilized IBX) 44 1,4-Benzoquinone 49

      cis-4-Benzyloxy-α,α-bis-(3,5-dimethylphenyl)-Lprolinol (2S,4R)- 52

      2,2_-Bipyrrolidines, (2S,2_S) and (2R,2_R) 54

      2-[Bis-[3,5-bis(trifluoromethyl)Phenyl] [(trimethylsilyl)oxy]Methyl]Pyrrolidine 57

      2,2-Bis[2-[4(S)-tert-butyl-1,3-oxazolinyl]]propane 59

      Bis[[(1R,1__R)-3,3__-[(1R,2R)-1,2-cyclohexanediylbis [(nitrilo-κN)methylidyne]]bis[2_-phenyl[1,1_-
      binaphthalen]-2-olato-κO]](2-)]di-μ-oxodi-titanium and Bis[[(1S,1__S)-3,3__-[(1S,2S)-1,2- cyclohexanediylbis[(nitrilo-κN)methylidyne]]bis [2_-phenyl[1,1_-binaphthalen]-2-olato-κO]](2-)]di- μ-oxodi-titanium 66

      Bis(2,2-dimethylpropanoato - κ-O)phenyl-iodine 69

      Bis(1-methyl-1-phenylethyl) Peroxide 77

      1,2-Bis(phenylsulfinyl)ethane 79

      N,N_-Bis(2,4,6-trimethylphenyl)imidazol-2-ylidene Palladium(I) Allyl Chloride 82

      Bis(trimethylsilyl) Peroxide 87

      Bromamine-T 91

      N-tert-Butyl-N-chlorocyanamide 94

      tert-Butyl Hydroperoxide 96

      tert-Butyl Hypochlorite 126

      tert-Butyl Peracetate 132

      Calcium Hypochlorite 137

      Chloramine-T 142

      Chlorobenzene 150

      Chloro[N,N_-ethylenebis(salicylideneaminato)] manganese 152

      Chromium(VI) Oxide 157

      Chromyl Acetate 163

      Cobalt, [5,10,15,20-tetraphenyl-21H,23Hporphinato( 2−)-κN 21,κN 22,κN 23,κN 24]- 167

      Cumyl Hydroperoxide 171

      N,N_-(1R,2R)-1,2-Cyclohexanediylbis- [N-hydroxy-α-phenybenzeneacetamide] 179

      1,5-Diaza-cis-decalin 183

      N,N-Dibromobenzenesulfonamide and N,N-Dibromo-p-toluenesulfonamide 188

      Di-μ-chlorobis(1,5-cyclooctadiene)diiridium(I) 195

      Di-μ-chlorodichlorobis[(1,2,3,4,5-η)-1,2,-3,4,5- pentamethyl-2,4-cyclopentadien-1-yl]diiridium 202

      (R)-2,10-Dichloro-5H-dinaphtho[2,1-g: 1,2-i][1,5]dioxacycloundecin-3,6,9(7h)-trione 210

      Dichloro(ethoxy)oxovanadium(V) 213

      1,1_-Difluoro-2,2_-bipyridinium Bis-(tetrafluoroborate) 217

      1,2:4,5-Di-O-isopropylidene-β-d-erythro-hexo-2,3- diulo-2,6-pyranose 221

      Di-μ-methoxobis(1,5-cyclooctadiene)diiridium(I) 224

      Dimethyldioxirane 228

      (S,S)-2,2_-(Dimethylmethylene)bis(4-tert-butyl-2- oxazoline) and (R,R)-2,2_-(Dimethylmethylene)bis- (4-tert-butyl- 2-oxazoline) 234

      Dispiro[2H-pyran-2,4_-[4H-5,6,8b]triazaacenaphthylene- 7_(5_H),2__-[2H]pyran], 1_,2_,2_a,3,3_,3__,4,4__,5,5__,
      6,6__,8_,8_a-tetradecahydro-1_,2_-dimethoxy-6,6__- dimethyl-, monohydrochloride, (1_S,2R,2_S,2__R, 2_aS,6S,6__S,8_aS)- 257

      N-fluoro-N-(phenylsulfonyl)-benzenesulfonamide 259

      N-Fluoropyridinium Tetrafluoroborate 270

      N-Fluoropyridinium Triflate 272

      1-Fluoro-2,4,6-trimethylpyridinium Tetrafluoroborate 274

      1-Fluoro-2,4,6-trimethylpyridinium Trifluoromethanesulfonate 278

      Hydrogen Peroxide 281

      Hydrogen Peroxide–Urea 295

      N-Hydroxyphthalimide 307

      Iodine 317

      2-Iodobenzenesulfonic Acid 332

      Iodosylbenzene 338

      Iridium, [N-[(1R,2R)-2-(amino-κN)-cyclohexyl]-4- methylbenzenesulfonamidato-κN]chloro[(1,2,3,4,5-η)-
      1,2,3,4,5-pentamethyl-2,4,- cyclopentadien-1-yl]-; Iridium, [N-[(1R,2R)-2-(amino-κN)- cyclohexyl]-4-
      methylbenzenesulfonamidato-κN]chloro[(1,2,3,4,5-η)- 1,2,3,4,5-pentamethyl-2,4,-cyclopentadien-1-yl]-; Iridium, [N-[(1S,2S)-2-(amino-κN)cyclohexyl]-4- methylbenzenesulfonamidato-κN]-chloro [(1,2,3,4,5-η)-1,2,3,4,5-pentamethyl-2,4,-
      cyclopentadien-1-yl]- 354

      Iridium, Dichlorodi-μ-hydrobis[(1,2,3,4,5-η)- 1,2,3,4,5-pentamethyl-2,4-cyclopentadien-1-yl]di- 357

      Iron, Bis(pyridine)bis(2-pyridinecarboxylato-N1,O2) 359

      Lithium Hydroperoxide 363

      Manganese(III) Acetate 367

      Manganese(II), bis(octahydro-1,4,7-trimethyl-1H-1,4,7- triazonine-κN1,κN4,κN7)tri-μ-oxodi-, hexafluorophosphate 375

      Manganese(II) tetraphenylporphyrin 378

      9-Mesityl-10-methylacridinium Perchlorate 381

      N-Methylmorpholine N-Oxide 384

      (S)-(−)-4-(2-Methylpropyl)-2-(2-pyridyl)-2-oxazoline 388

      Methyl(trifluoromethyl)dioxirane 390

      Methyltrioxorhenium 396

      Molybdenum Chloride Oxide 407

      Noyori Oxidation (Sodium Tungstate Dihydrate, Hydrogen Peroxide, Methyltri-n-octylammonium Hydrogen Sulfate, Phosphonic Acid) 411

      3,3_,3α,3α _,4,4_,5,5_-Octahydro-3,3,3_,3_-tetraisopropyl- 6,6_-spirobi-[6H-cyclopent[c]isoxazole] 415

      4,4,4_,4_,5,5,5_,5_-Octamethyl-2,2_-bi-1,3,2-dioxaborolane 421

      Osmium Tetroxide 433

      μ-Oxo-bis[tetrakis(t-butyl)-phthalocyaninatoiron(III)] 452

      Oxygen 454

      Palladium (II) Sparteine Dichloride 467

      Peracetic Acid 470

      (8α,9R)-(8__ α,9__R)-1,1__-[1,3-Phenylene-bis(methylene)] bis[9-hydroxy-cinchonanium] Dibromide and (9S)-(9__S)-1,1__-[1,3-Phenylene-bis(methylene)] bis[9-hydroxy-cinchonanium]Dibromide 478

      (−)(1S)-1-Phenylethyl Hydroperoxide and (+)(1R)-1-Phenylethyl Hydroperoxide 480

      (8α,9R)-(8__ α,9__R)-9,9__-[1,4-Phthalazinediylbis(oxy)] bis[10,11-dihydro-6_-methoxycinchonan] & (9S)-(9__S)-9,9__-[1,4-Phthalazinediylbis(oxy)] bis[10,11-dihydro-6_-methoxycinchonan] 483

      Picolinic Acid 495

      Polyaniline 498

      Potassium Bromate 502

      Potassium Monoperoxysulfate 506

      2-Pyrazinecarboxylic Acid 524

      2,3-Pyrazinedicarboxylic Acid 530

      Pyrrolidine, 3,4-bis(diphenylphosphino)-1- (phenylmethyl)-,(3R,4R) and Pyrrolidine, 3,4-bis(diphenylphosphino)-1-(phenylmethyl)-, (3S,4S) 532

      2-Pyrrolidinemethanol-α,α-bis(3,5-dimethylphenyl)- (2S); and 2-Pyrrolidine-methanol-α,α-bis(3,5- dimethylphenyl)-(2R) 535

      Rhenium(VII) Oxide 541

      [RuCl2(p-cymene)2]2 546

      Ruthenium(III) Chloride 549

      Ruthenium Complex of N,N_,N_-Trimethyl-1,4,7-triazacyclononane and Ruthenium Complex of cis-Diaquabis
      (6,6_-Dichloro-2,2_-bipyridine) 561

      Ruthenium Dodecacarbonyltri Triangulo 565

      Ruthenium Hydroxide 568

      Selenium(IV) Oxide 575

      Sodium Bromate 583

      Sodium Hypochlorite 587

      Sodium Hypochlorite–N,N_-Bis(3,5-di-tertbutylsalicylidene)- 1,2-cyclohexanediaminomanganese( III) Chloride 600

      Spiro[6H-1,3-dioxolo[4,5-c]pyran-6,5_-oxazolidine]-3_- carboxylic acid, tetrahydro-2,2-dimethyl-2_,7- dioxo-,2-methyl-2-propyl ester, (3aR, 5_S, 7aR)- 604

      Tetrabutylammonium Bis(pyrazinecarboxylato)- dioxo-vanadium(V) 609

      Tetrabutylammonium Dodecatungstophosphate 611

      Tetrabutylammonium Peroxydisulfate 615

      5,6,7,8-Tetrafluoro-1-hydroxy-1-oxobenziodoxol- 3(1H)one (Tetrafluoro-IBX) 618

      2,2,6,6-Tetramethylpiperidin-1-oxyl 620

      Tetra-n-propylammonium Perruthenate 626

      3,3_,5,5_-Tetra-tert-butyldiphenoquinone 630

      (S)-2-(5-1H-Tetrazolyl)pyrrolidine and (R)-2-(5-1H-Tetrazolyl)pyrrolidine 633

      4,4_,4__-tri-tert-butyl-2,2_:6_,2__-terpyridine 639

      Trichloroisocyanuric Acid 642

      Trifluoroperacetic Acid 649

      Trimethylamine N-Oxide 659

      Triphenylmethyl Hydroperoxide 667

      Tris(2-pyridylmethyl)amine 670

      Tris[4-(trifluoromethyl)phenyl]phosphine 677

      Vanadium,bis[N-[(1S)-1-(carboxy-κO)ethyl]-N- (hydroxy-κO)-l-alaninato(2-)-κN,κO]- 681

      Vanadyl Bis(acetylacetonate) 684

      List of Contributors 693

      Reagent Formula Index 707

      Subject Index 711

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