Catalytic Oxidation Reagents (eBook, PDF)
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The Handbook is part of the Handbook of Reagents for Organic Chemistry series, aiming at collecting articles on a particular theme that individual researchers in academia or industry can use on a daily basis. The Handbook starts with a section discussing the most important aspects of heteroarene functionalization. The introduction is followed by the alphabetical listing of the most relevant reagents drawn from the EROS database. The Editor, Andre Charette from the University of Montreal, has selected 120 reagent descriptions, many of them updated with heteroarene-specific reactions for this…mehr
- Geräte: PC
- eBook Hilfe
The Handbook is part of the Handbook of Reagents for Organic Chemistry series, aiming at collecting articles on a particular theme that individual researchers in academia or industry can use on a daily basis. The Handbook starts with a section discussing the most important aspects of heteroarene functionalization. The introduction is followed by the alphabetical listing of the most relevant reagents drawn from the EROS database. The Editor, Andre Charette from the University of Montreal, has selected 120 reagent descriptions, many of them updated with heteroarene-specific reactions for this Handbook. Following the standard format for EROS, each article contains an overview of the synthesis and physical properties of the reagents or catalyst, conditions for its storage, and purification methods. Given the importance of heteroarenes in biology and especially in medicinal chemistry, a Handbook that focuses exclusively on heteroarene functionalization has been long overdue. This Handbook will have a broad appeal to many individuals engaged in the area of medicinal chemistry, fine chemical synthesis and industrial-scale chemistry. Key features: * Builds on the success of the previously published Handbooks of Reagents for Organic Synthesis * Compares the numerous new C-H functionalization reactions that have been developed in the past decade * Heteroarene functionalization is widely used in the development of pharmaceuticals and other bioactive compounds * Contains listings of secondary reagents for which more information is available in the online edition
Produktdetails
- Produktdetails
- Verlag: John Wiley & Sons
- Seitenzahl: 792
- Erscheinungstermin: 29. Juli 2013
- Englisch
- ISBN-13: 9781118704820
- Artikelnr.: 39287398
- Verlag: John Wiley & Sons
- Seitenzahl: 792
- Erscheinungstermin: 29. Juli 2013
- Englisch
- ISBN-13: 9781118704820
- Artikelnr.: 39287398
Professor Philip L. Fuchs, Department of Chemistry, Purdue University Philip 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
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
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
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
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
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