Handbook of Reagents for Organic Synthesis
Catalytic Oxidation Reagents
Handbook of Reagents for Organic Synthesis
1. Edition September 2013
782 Pages, Hardcover
Wiley & Sons Ltd
Short Description
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. It 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 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
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-alpha,alpha-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-kappaN)methylidyne]]bis[2_-phenyl[1,1_-
binaphthalen]-2-olato-kappaO]](2-)]di-mu-oxodi-titanium and Bis[[(1S,1__S)-3,3__-[(1S,2S)-1,2- cyclohexanediylbis[(nitrilo-kappaN)methylidyne]]bis [2_-phenyl[1,1_-binaphthalen]-2-olato-kappaO]](2-)]di- mu-oxodi-titanium 66
Bis(2,2-dimethylpropanoato - kappa-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.)-kappaN 21,kappaN 22,kappaN 23,kappaN 24]- 167
Cumyl Hydroperoxide 171
N,N_-(1R,2R)-1,2-Cyclohexanediylbis- [N-hydroxy-alpha-phenybenzeneacetamide] 179
1,5-Diaza-cis-decalin 183
N,N-Dibromobenzenesulfonamide and N,N-Dibromo-p-toluenesulfonamide 188
Di-mu-chlorobis(1,5-cyclooctadiene)diiridium(I) 195
Di-mu-chlorodichlorobis[(1,2,3,4,5-eta)-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-ß-d-erythro-hexo-2,3- diulo-2,6-pyranose 221
Di-mu-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-kappaN)-cyclohexyl]-4- methylbenzenesulfonamidato-kappaN]chloro[(1,2,3,4,5-eta)-
1,2,3,4,5-pentamethyl-2,4,- cyclopentadien-1-yl]-; Iridium, [N-[(1R,2R)-2-(amino-kappaN)- cyclohexyl]-4-
methylbenzenesulfonamidato-kappaN]chloro[(1,2,3,4,5-eta)- 1,2,3,4,5-pentamethyl-2,4,-cyclopentadien-1-yl]-; Iridium, [N-[(1S,2S)-2-(amino-kappaN)cyclohexyl]-4- methylbenzenesulfonamidato-kappaN]-chloro [(1,2,3,4,5-eta)-1,2,3,4,5-pentamethyl-2,4,-
cyclopentadien-1-yl]- 354
Iridium, Dichlorodi-mu-hydrobis[(1,2,3,4,5-eta)- 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-kappaN1,kappaN4,kappaN7)tri-mu-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_,3alpha,3alpha _,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
mu-Oxo-bis[tetrakis(t-butyl)-phthalocyaninatoiron(III)] 452
Oxygen 454
Palladium (II) Sparteine Dichloride 467
Peracetic Acid 470
(8alpha,9R)-(8__ alpha,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
(8alpha,9R)-(8__ alpha,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-alpha,alpha-bis(3,5-dimethylphenyl)- (2S); and 2-Pyrrolidine-methanol-alpha,alpha-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-kappaO)ethyl]-N- (hydroxy-kappaO)-l-alaninato(2-)-kappaN,kappaO]- 681
Vanadyl Bis(acetylacetonate) 684
List of Contributors 693
Reagent Formula Index 707
Subject Index 711
