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Handbook of Reagents for Organic Synthesis: Catalytic Oxidation Reagents

Philip L. Fuchs (Editor)
ISBN: 978-1-119-95327-2
782 pages
October 2013
Handbook of Reagents for Organic Synthesis: Catalytic Oxidation Reagents (1119953278) cover image

The Handbook of Reagents for Organic Synthesis: Catalytic Oxidation Reagents is part of the Handbook for Reagents for Organic Synthesis series, making use of the leading reagent database e-EROS. It provides concise and informative articles written by experts in the area and provides comprehensive referencing to the original literature.  As is the standard format for EROS, each article also contains an overview of the synthesis and physical properties of the catalysts, conditions for its storage, and purification methods. 

The Handbook compiles essential reagents in this area, starting with an introductory section discussing the main classes of oxidation catalysts, followed by an alphabetical list of reagents, with an attempt to keep families of catalysts organized by related chemistry for ease of use. The Handbook concludes with a list of contributors and a detailed index.

The Handbook of Reagents for Organic Synthesis: Catalytic Oxidation Reagents if of interest for everyone engaged in the area of sustainable chemistry, fuel alternatives research for the generation of energy, and synthetic chemists working in pharmaceutical industries and medicinal chemistry.

Key features:

  • Builds on the success of the previously published Handbooks of Reagents for Organic Synthesis
  • Oxidations are the most frequently used steps in organic synthesis
  • Catalysts for oxidation reactions are the key for green or sustainable chemistry
  • Oxidation, the addition of oxygen to biomolecules, is key for the metabolism of humans and animals
  • Oxidations of carbohydrates from simple organic compounds are the key for new renewable energies
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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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