Catalytic Oxidation Reagents

Professor Philip L. Fuchs, Department of Chemistry, Purdue UniversityPhilip Fuchs began his career at Purdue in 1973. Since that time, he has graduated an extended family of 55 Ph.D.s. His awards and honors include an Eli Lilly young faculty fellowship (1975), an Alfred P. Sloan fellowship (1977), a Pioneer in Laboratory Robotics award (1986), a Martin teaching award (1991), and being voted by the students as one of Top 10 Teachers in School of Science at Purdue (1991, 1993, 1995, 1996).Fuchs has consulted for Pfizer, and Eli Lilly, served on the editorial board of The Journal of Organic Chemistry, and is currently an executive editor for the Electronic Encyclopedia of Organic Reagents (e-EROS), an online dynamic encyclopedia published by John Wiley & Sons.

• 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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