Baeckvall J.-E. (ed.) Modern Oxidation Methods
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benzenedicarbaldehyde 217
benzeneseleninic acid 132
benzoic acid 194, 205
benzyl alcohol
– [Cu(II)BSP]-catalyzed aerobic
oxidation 171
benzyl phenyl selenide 9
benzylic compound 201
benzylidenecyclopropane 95
benzyltriphenyl phosphonium
peroxymonosulfate 279
(R)-BINAP 285
biocatalytic oxidation 306
biocatalytic reaction 298
biooxidation
– cytochrome P450 monooxygenase 421ff.
biotin
– biosynthesis pathway 427
– vanadyl ion 297
2,2
0
-bipyridine (Bpy, bipy) 170ff.
bisacetoxyiodo benzene [PhI(OAc)
2
]76
(S,S)-1,2-bis-
t
butyl-1,2-ethanediol 296
bis-(picolyl)(N-methylimidazol-2-yl)amine
(bpia) 374
bis-pyridyl-cyclohexane-1,2-diamine based
ligand
– chiral 412
1,4-bis(9-0-quininyl)phthalazine
[(QN)
2
PHAL] 23
bis-trimethylsilyl peroxide (BTSP) 60
bistetrahydrofuran C17-C32 fragment 100f.
bleaching
– Mn-catalyzed 375
[BMIm]PF
6
291ff., 308
BPMEN (N,N
0
-dimethyl-N,N
0
-bis(2-
pyridylmethyl)-diaminoethane) 65f.
– [(BPMEN)Fe(CH
3
CN)
2
](OTf)
2
67
– (BPMEN)Fe(SbF
6
)
2
30
brassinolide 428
brevitoxin B 107f.
bromoperoxidase (VBrPO)
– V-containing 299
bromotriterpene polyether 101
BSP 170
BTX (benzene, toluene, xylene) aromatics
11
bufuralol 436
buspirone 442
a,b-butenolide 223
tert-butoxymethyltoluene 217
tert-butyl benzyl ether 217
(10R,3S)-3-[10-(tert-butyldimethylsilyloxy)
ethyl]azetidin-2-one 262
a-(tert-butyldioxy)alkylamine 255
4-(tert-butyldioxy)-4-
alkylcyclohexadienone 263
a-tert-butyldioxyamine 256
a-t-butyldioxypyrrolidine
– TiCl
4
-promoted reaction 260
tert-butyl hydroperoxide (TBHP) 39, 325
tert-butyl nitrite (t-BuONO) 219
c
D-(þ)-camphor 440
– stereospecific hydroxylation 426
(1R)-(þ)-camphor 438
e-caprolactam (CL) 210
– precursor 210ff.
e-caprolactone 139, 209
carbapenem 262
carbon dioxide
– supercritical 343
carbon monoxide 212
carbon radical generation 222
carbon radical-producing catalyst
(CRPC) 188, 229
carbon-carbon bond-forming reaction 222,
257
carbonyl compound
– oxidation 353ff.
4-carboxybenzaldehyde (4-CBA) 198
carboxylation 212
– alkane 212
carboxylic acid 353
– metal-free oxidation of aldehyde 354
2-(carboxy)phenyl methyl sulfide 299
2-(carboxy)vinyl methyl sulfide 299
castasterone 428
catalyst
– development 86
– heterogeneous 46
– homogeneous 42
catechol
– Ru-catalyzed oxygenation 264
cerium ammonium nitrate (CAN)
– Ritter-type reaction 220f.
cetylpyridinium chloride 178
chemocatalytic oxidation 302
chemocatalytic reaction 280
Chimassorb 944 149
S,S-Chiraphos 77
chlorite 8
m-chlorobenzoic acid (MCBA) 205
chlorohydrin process 37
m-chloroperbenzoic acid (m-CPBA) 382
chloroperoxidase (CPO) 298
4-chlorostyrene 75
chromenes
Index
j
453
– epoxidation 93
chromium
– CrO
3
(pyridine)
2
204
– CrO
3
/TBH 204
cobalt
– Co(II) 196
– Co(II) 2-ethylhexanoate 194
– Co(II) Schiff base complex 76
– Co(III) acetate 189
– [Co(III)W
12
O
40
]
5
334
– Co(acac)
3
175
– [Co
4
(H
2
O)
2
P
2
W
18
O
68
]
10
319
– Co/Mn/Br system 198
– Co(OAc)
2
191ff.
– Keggin-type polyoxometalate 333
– [PCo(II)Mo
11
O
39
]
5
334
– [PCo(H
2
O)W
11
O
39
]
5
319
– Schiff-base complex 305
cofactor substitution and regeneration 438f.
compactin 432
copper
– Cu(I) 173
– [Cu
II
(bipyridine ligand)] complex 174
– Cu
II
Br
2
(Bpy)–TEMPO 174
– [Cu(II)BSP] 170
– Cu(acac)
2
204
– CuCl
2
/phenanthroline catalyst 205
– Cu(OAc)
2
191
– oxidation with O
2
170
Coprinus cinerem peroxidase (Cip) 299
cortisone acetate 248
cryptophycin 52 99
cumene-phenol process 202
cyanation
– oxidative 257
cyanohydrin 250
N-cyanomethyl-N-methylaniline
– TiCl
4
-promoted reaction 257
3-cyanopyridine 57
4-cyanopyridine 305
cycloalkane
– nitrosation with t-BuONO 219
cycloalkanone 209
cyclodecanone monoxygenase (CDMO) 360
cyclododecanone monooxygenase (CDMO)
299
cyclohexane 267
cyclohexanone 136
cyclohexanone monooxygenase (CHMO)
299ff., 359f.
– Acinetobacter sp. (CHMO
Acineto
) 359
cyclohexylbenzene 202
cyclohexylbenzene-1-hydroperoxide
(CHBH) 202
cyclooctane 267
cyclooctene 66
– epoxidation 27, 45
cis-cyclooctene
– Mn-porphyrin catalyzed epoxidation 48
Z-cyclooctene 123
cyclopentadecanone monoxygenase
(CPDMO) 360
cyclopentanone monoxygenase (CPMO) 299,
360
cyclophosphamide 436
cytochrome P450 monooxygenase 332, 421ff.
– artificial fusion protein 440
– Bacillus megaterium 442
– biocatalysis 438
– biooxidation 421ff.
– catalytic cycle 424
– catalyzed reaction 425
– cofactor substitution and regeneration 438
– CYP1A2 435
– CYP102A1 425
– CYP102A2 425, 443
– CYP102A3 425, 443
– CYP107A1 433
– CYP107H1 427
– CYP170A1 433
– CYP2C9 435
– CYP3A4 435
– CYP51 427
– CYP505A1 425
– engineering 430ff.
– enzymology 423
– functional multi-domain protein 436
– fusion protein 436
– industrial application 430
– industrial biocatalyst 429
– mammalian 434
– pharmaceutical synthesis 431
– Pseudomonas putida 440
– recombinant expression in Escherichia
coli 435
– selectivity 436
– structure 422f.
– substrate specificity 440
– synthesis of fine chemicals 437
– technical application 429
d
DBAD (dibutylazodicarboxylate) 171f.
DEAD-H
2
(diethylazo dicarboxylate) 172
2-decanone 136
1-decene 134
(E)-5-decene 241
trans-5-decene 66ff.
454
j
Index
cis-dec-4-enoic acid
– epoxidation with ketone 96
4-demethoxyadriamycinone 248
demethylation 427
N-demethylation
– tertiary amine 256
O-demethylation
– 7-methoxyresorufin 436
– 5-methoxytryptamine 428
11-deoxycortisol 431
1-deoxy-5-hydroxy-sphingolipid analog 100
dextromethorphan 436
diacetoxyiodosylbenzene 249
3b, 21-diacetoxy-5a-pregn-17-ene 248
dialkoxyruthenium(IV) complex 161
dialkoxyruthenium(IV)-tmp complex 160
1,2-diaminocyclohexane 66
dibenzoyl peroxide (BPO) 227
1,3-di-tert-butoxymethylbenzene 217
di-tert-butyl hyponitrite (TBHN) 227
di-n-butylphenylarsine 129f.
2,6-dichloropyridine N-oxide (2,6-DCPNO)
74, 193
diclofenac 435
cis-dienes 96
– epoxidation with ketone 96
(R,R)-diethyl tartrate ((R,R)-DET) 296
(S,S)-diethyl tartrate ((S,S)-DET) 297
difluoro flavin 291
1,2-dihaloalkene 243
1,3-dihydro-2-benzofuran 217
2,3-dihydrobenzo[b]thiophene 299
1,2-dihydronaphthalene 384
1,1
0
-dihydroxydicyclohexyl peroxide 210
(R)-2,3-dihydroxy-2,3-dihydrosqualene 105
a,a-dihydroxyketone 244
dihydroxylation
– alkene 1ff., 307
– biomimetic 307
– metal-catalyzed 1ff.
– Os-catalyzed 2ff.
– Ru catalysis 24f.
cis-dihydroxylation
– alkene 375, 396
N,N-dihydroxypyromellitimide (NDHPI)
191
2,6-diisopropylnaphthalene 203
a-diketone 243
1,4-dimethoxymethylbenzene 218
1,3-dimethyladamantane 212ff.
N,N-dimethylamino derivative 303
N,N-dimethylaniline 428
2,2-dimethylchromene 403
dimethyldioxirane (DMD) 301
(S)-(N,N-dimethyl)-1-phenylethylamine 64
dimethyl tacn (dmtacn) 395
dimethyl terephthalate (DMT) 196
4,11-dimethyl-1,4,8,11-tetraazabicyclo[6.6.2]
hexadecane (Me
2
EBC) 386
1,3-dinitroadamantane 214
diol
– oxidation with dioxygen 206f.
dioxirane 86, 278
1,3-dioxolane 224
dioxygen
– hydroxyacylation 224
– oxidation 188, 206f.
– oxyalkylation of alkene 222
– terminal oxidant 293
dioxygenase mechanism 340
diphenylmethylamine 258
diselenide/seleninic acid 132
disulfide
– oxidation of thiol and thiophenol 138
1-dodecene 66
drug development
– mammalian cytochrome P450 434
e
early transition metal
– epoxidation of alkene 39
electron transfer mediator (ETM) 3f.
enantioselective catalyst 228
endo-oxacyclization 106
(þ)-enshuol 102
cis-enyne
– epoxidation with ketone 96
epibatidine 225
epi-isozizaene 433
epothilone 99, 426
– B 426
– D 426ff.
epoxidation
– alkene 37ff., 91ff., 123ff., 208, 375ff.,
392
– allylic alcohol 331
– asymmetric, see asymmetric epoxidation
– cyclooctene 27, 45
– dioxygen 208
– enantioselective 393
– ethene with H
2
O
2
128
– Fe-catalyzed 64ff.
– fluorinated alcohol solvent 123
– 1-hexene 389
– H
2
O
2
123ff., 387
– late transition metal 76
– mechanism of catalysis by fluorinated
alcohol 123
Index
j
455
– metalloporphyrin-promoted 247
– Mn-catalyzed 47
– Mn-tptn catalyst 405
– Mo-catalyzed 42
– MTO-catalyzed 56
– oxidant 38
– radical-type pathway 406
– Re-catalyzed 52
– Ru-catalyzed 74f., 243
– sandwich-type POM-catalyzed 331
– selective 38
– synthetic application 98f.
– transition metal-catalyzed 37ff., 80
– transition state 92ff.
– W-catalyzed 42
epoxide cyclization 107
epoxide rearrangement 94f.
cis- and trans-2,3-epoxyoctane 209
erythromycin 433
esomeprazol 296f.
ester
– oxidation of ketone 138
– unsaturated 223
ethane
– epoxidation with H
2
O
2
128
1-ethyl-3-methylimidazolium
tetrafluoroborate 62
5-ethyl-2-methylpyridine 200
2-ethylanthraquinone (EAQ)/2-
ethylanthrahydroquinone (EAHQ)
process 46
ethylbenzene hydroperoxide (EBHP) 39
o-ethyltoluene 194
f
FAD-containing monooxygenase
(FADMO) 286ff.
flavin 4
– catalyst 287f.
– chiral 291f.
flavin adenine dinucleotide (FAD) 358
flavin hydroperoxide 3, 294
flavin mononucleotide (FMN) 358
flavoenzyme 295
flavoprotein monooxygenase 358
fluorinated alcohol 118f.
– Baeyer-Villiger oxidation of ketone 136ff.
– epoxidation of alkene 123
– mechanism of epoxidation catalysis 123
– sulfoxidation of thioether 136
fluoroketone
– catalyst 135
fluorous phase
– H
2
O
2
117, 279
g
giant Pd cluster 163ff.
glabrescol 105
(þ)-glisoprenin A 105f.
3-(glycidyloxy)propyltrimethoxysilane 395
glyoxylic acid methylester methyl hemiacetal
(gmha) 397f.
gold
– HAuCl
4
/AgNO
3
294
– nanoparticle 169
h
H-bond enhanced H-bonding 119
haloperoxidase 298
heptanoic acid 207
heterocyclic additive 55
N-heterocyclic carbene-catalyzed (NHC-
catalyzed) oxidative transformation 354
heterogenization
– homogeneous reaction 341
heterogeneous catalyst 46
heteropoly acid
– Keggin type 324
heteropolyoxometalate 189
hexafluoroacetone 135
hexafluoro-2-propanol 61
1,1,1,3,3,3-hexafluoro-2-propanol (HFIP)
117ff, 279
– aggregation-induced H bonding
enhancement 122
– H bond donor feature 120
1-hexene
– epoxidation 389
Hock process 202
homogeneous catalyst 42
hydroacylation 224ff.
hydroaromatic compound 201
hydrocarbon
– oxidation 265f.
hydrocortisone 431
hydrogen bond
– low-barrier 126
hydrogen bond donor feature
– HFIP 120
hydrogen peroxide 3, 46
– alkene epoxidation 123
– catalytic oxidation in fluorinated alcohol
solvent 117ff., 279
– catalytic oxidation of alcohol 176
– decomposition 373
– epoxidation 387
– epoxidation of ethene 128
– fluorous phase 279
– manganese catalase 373
456
j
Index
– Mn-catalyzed oxidation 371ff.
– terminal oxidant 42, 280
a-hydroperoxyethylbenzene 201
2-hydroperoxy-2-hydroxypropane (hhpp) 388
hydroquinidine 1,4-phthalazinediyl diether
(DHQD)
2
PHAL 4ff.
hydrotalcite 169
– Ni-substituted 176
– Ru-exchanged (Ru-HT) 162
4-hydroxyacetophenone monooxygenase
(HAPMO) 299, 360
hydroxyacylation 224f.
hydroxyapatite 168f.
4-hydroxybenzoate 440
o-hydroxycaproic acid 139
a-hydroxy carbon radical 223
4-hydroxydiclofenac 435
a-hydroxy-c,c-dimethyl-c-butyrolactone 223
1-hydroxy-1-hydroperoxycyclohexane 210
N-hydroxyimide 205
a-hydroxyketone 248
a-hydroxy-c-lactone 223
hydroxylation
– D-(þ)-camphor 426
– diastereoselective 437
– pyridylhomothreonine 426
– regioselective 437ff.
– stereoselective 441
N-hydroxyphthalimide (NHPI) 175, 187ff.,
229, 294
– carbon-carbon bond-forming reaction 222
– chiral derivative 228
– fluorinated 190
– functionalization of alkane 212
– NHPI/CAN system 220f.
– NHPI-catalyzed aerobic oxidation 188
– NHPI/Co(II) system 205, 222
– NHPI/Co(acac)
2
system 193
– NHPI/Co(OAc)
2
system 189ff., 205
– NHPI/Cu(II) system 204
– NHPI/NO
2
system 214
– polarity reversal catalyst 226
a-hydroxy-c-spirolactone 224
6b-hydroxytestosterone 435
hypochlorite 5, 148, 382
hypochlorite-procedure 7
i
idarubicin 248
ifosfamide 436
indole 260
inorganic metalloporphyrin 318
o-iodooxybenzoic acid (IBX) 298
iodosyl benzene 76, 249, 382
ionic interaction
– immobilization 21
ionic liquid 22, 254, 299ff.
– aerobic Ru-catalyzed oxidation 153
– H
2
O
2
-based sulfoxidation 291
– heterogeneous catalytic oxidation of
sulfide 292
a-ionone 437
b-ionone 437ff.
iron
– Fe(III)-OOH intermediate 324
– FeCl
3
189
– [Fe
2
Ni(OAc)
3
PW
9
O
37
]
10
333
– Fe(NO
3
)
3
-FeBr
3
294
– (MEP)Fe(SbF
6
)
2
30
– polyfluorinated Fe(TPP)-catalyst 65
– [(TPA)Fe(CH
3
CN)
2
](OTf)
2
(TPA¼
trispicolylamine) 67
iron catalyst 26
– asymmetric epoxidation 72
– epoxidation 64ff.
iron complex
– chiral 31
iron porphyrin 64
iron-oxo species 321
isophthalic acid 194
isoquinoline 260
j
Jacobsen-catalyst 50
Julia-Kocienski alkenation 100
k
K, see potassium
KA oil 187ff., 209ff.
– Baeyer-Villiger oxidation 209
Keggin-type compound 318ff.
Keggin-type silicodecatungstate
[c-SiW
10
O
34
(H
2
O)
2
]
4
44
ketone 86, 267
– acetylenic 204
– ammonium 87
– N-aryl-substituted 93
– Baeyer-Villiger oxidation in fluorinated
alcohol solvent 136ff.
– bicyclo[3.2.1]octan-3-ones 88
– bis(ammonium) 87
– C2-symmetric binaphthyl-based 87
– carbocyclic 86
– carbohydrate-based 88
– chiral 89
– epoxidation of alkene 97
– epoxidation of trans and trisubstituted
alkenes 91
Index
j
457
– fructose-derived 87
– oxidation 356
– oxidation to lactone and ester 138
ketone monooxygenase 299
ketone-catalyzed asymmetric epoxidation
– alkene 85ff.
l
b-lactam 260f.
– acyloxylation 261
– aerobic oxidation 262
lactone 108, 209
– oxidation of ketone 138
lanosterol
– demethylation 427
lanthanide
– catalyst 286
lauric acid 206
layered double hydroxide (LDH) 21, 46, 281
– W-exchanged Mg-Al 303
limonene 434ff.
(4R)-limonene 442
lipophiloselective oxidation 345
liquid-liquid reaction system 341ff.
liquid phase catalysis
– solvent-anchored supported 343
liquid phase oxidation
– polyoxometalate-catalyzed 315ff.
lithium
– LiNbMoO
6
285
()-longilene peroxide 100f.
low-barrier hydrogen bond 126
m
magnesium
– Mg
6
Al
2
Ru
0.5
(OH)
16
CO
3
162
manganese
– alkene oxidation 405
– bleaching 375
– bio-inspired oxidation catalyst 372
– manganese sulfate/H
2
O
2
system 51
– [Mn
III
2
O(m-O)(m-RCO
2
)
2
(tmtacn)
2
]
2þ
complex 402f.
– Mn(III) porphyrin/Pt/H
2
system 188
– Mn(III) tetra-2,6-
dichlorophenylporphyrin 318
– Mn(III)(salen) complex 285, 410f.
– [Mn
IV
2
(m-O)
3
(tmtacn)
2
]
2þ
399ff.
– Mn(acac)
2
189
– Mn(Me
2
EBC)Cl
2
386
– Mn(OAc)
2
200
– Mn(OAc)
3
407
– Mn(OAc)
3
.
2H
2
O 282
– [Mn
2
O(OAc)(tmtacn)
2
](PF
6
)
2
387
– [(Mn
2
O(OAc)
2
tptn)]
2þ
405f.
– [Mn
2
O
3
(TMTACN)]
2þ
50
– [Mn
2
O
3
(tmtacn)
2
](PF
6
)
2
375, 397ff.
– Mn-porphyrin complex 379
– Mn(salen) complex 298, 382ff.
– Mn-tmtacn complex 395ff., 407ff.
– Mn-tmtacn derivative on solid suport 395
– Mn-tmtacn/oxalate system 389f.
– Mn(TPP)Cl 49
– Mn-tptn catalyst 405
– oxidation of alkane, alcohol and
aldehyde 407
– ozonide complex 320
– [PMn(H
2
O)W
11
O
39
]
5
319
– [P
2
Mn(H
2
O)W
17
O
61
]
7
319
– salt 376
manganese-catalyzed epoxidation 47
– porphyrin 48
manganese-catalyzed oxidation
– H
2
O
2
371ff.
manganese-substituted polyoxometalate 320
– sandwich structure 321
Mars–van Krevelen-type mechanism 338
maytenine 250
MCM-41 149, 159f.
– catalyst 46
(MEP)Fe(SbF
6
)
2
30
()-mesembrine 100f.
metal-mediated oxidation of alcohol 151, 174
metalloenzyme 297
metalloporphyrin 378
metalloporphyrin-promoted epoxidation 247
metallosalen compound 339
methane
– aerobic oxidation 339
methane monooxygenase (MMO) 30, 65, 332
1-(methoxycarbonyl)pyrrolidine
– Ru-catalyzed oxidation 260
a-methoxylation
– tertiary amine 256
4-methoxymethyltoluene 217
1-(4-methoxyphenyl)-1-phenylethane 203
7-methoxyresorufin 436
5-methoxytryptamine 428
N-methylamine 256
– oxidation 256
3-methyl-2-butanone 252
1-methylcyclohexane 247
methyl 3-(3,3
0
-dimethyladamantyl)-2-
hydroxypropionate 223
methyl 3-(3,3
0
-dimethyladamantyl)-2-
oxopropionate 223
N-methyl-N-(3-heptenyl)aniline 256
N-methylhomoallylamines 256
458
j
Index
N-methylmorpholine (NMM) 3f., 306f.
N-methylmorpholine N-oxide (NMO) 2f.,
157, 249ff., 306, 384
2-methyl-1,4-naphthaquinone 337
2-methyl-1-naphthol 337
methylpyridine 199
3-methylpyrazole 58
methylquinoline 199
3-methylquinoline 200
a-methylstyrene 10ff.
– Os-catalyzed dihydroxylation 4ff.
– Ru-catalyzed dihydroxylation 24
cis-b-methylstyrene 64, 90, 406
– epoxidation 93
trans-b-methylstyrene 72
methyl thioglycolate 227
methyltrioctylammonium chloride 177
methyltrioxorhenium (methylrhenium trioxide,
MTO) 3f., 52ff., 79, 133, 178, 305, 307
– asymmetric epoxidation 64
– epoxidation catalyst 54
– oxidation catalyst 133
– solvents/media 61
metoprolol 436
microbial oxidation
– P450 for pharmaceutical synthesis 431
microencapsulated osmium tetroxide (MC
OsO
4
) 17ff.
molybdenum
– epoxidation 42
– H
5
PV
2
Mo
10
O
40
335ff.
– Mo(VI) peroxo complex 177
– Ph
2
PO
2
[MoO(O
2
)
2
]
2
281
– [PPh
4
][Mo(O)(O
2
)
2
(QO)] 45
– [PV
2
Mo
10
O
40
]
5
336ff.
– [PZnMo
2
W
9
O
39
]
5
polyoxometalate 328
– Q
3
PMo
12
O
40
281, 322
– Q
5
[PV
2
Mo
10
O
40
](Q¼quaternary
ammonium cation) 328
mono-oxygen donor 317
– oxidation 317
MTO, see methyltrioxorhenium
myrtenol 439
n
NADH 439
ent-nakorone 103f.
nano-iron 178
nano-cluster
– Pd 168
naphthalene 441
naphthalene derivative
– oxidation 264
2,6-naphthalenediol 203
naphthoquinone 264
NADPH 299f., 359, 438
NAPI, see N-acetoxyphthalimide
NDHPI, see N,N-dihydroxypyromellitimide
Nexium
Ò
296
NHPI, see N-hydroxyphthalimide
NHPI/CAN system 220f.
NHPI-catalyzed aerobic oxidation 188
NHPI/Co(II) system 205, 222
NHPI/Co(acac)
2
system 193
NHPI/Co(OAc)
2
system 189ff., 205
NHPI/Cu(II) system 204
NHPI/NO
2
system 214
nickel-substituted hydrotalcite 176
nicotinic acid 200
(þ)-nigellamine A
2
102
nikkomycin 426
nitration
– alkane with NO
2
212
nitric oxide
– reaction with organic compound 217
nitrile
– Ru-catalyzed oxidation 266
nitroadamantane 214
nitroalkane 213
nitrogen-group donating support 16
nitrone 258
nitrosation
– cycloalkane with t-BuONO 219
NMO, see N-methylmorpholine N-oxide
2-nonanone 136
nootkatol 437f.
(þ)-nootkatone 437f.
norbornane
– fused 245
o
1,2-octanediol 207
2-octanone 136
1-octene 134
cis-2-octene 209
trans-2-octene 68, 209, 406
trans-4-octene 406
4-octyn-3-ol 204
4-octyn-3-one 204
4-octyne 204
(þ)-omaezakianol 102
omeprazol 297
organometallic polymer 63
osmium
– dihydroxylation 2ff.
– microencapsulated osmium tetroxide
(MC OsO
4
) 17ff.
– Os EnCat
Ò
19
Index
j
459
– osmium tetroxide 20
– osmium(VI) glycolate 2
– osmium(VI) mono(glycolate) 8
– osmium(VIII) mono(glycolate) 8
osmium catalyst 16ff.
– polyaniline 16
– supported 16
osmylation
– alkene 2
endo-oxacyclization 106
oxazolidine 228
– kinetic resolution 228f.
oxidant
– environmentally friendly terminal 3
– epoxidation 38
– hypochlorite 148
– terminal, see terminal oxidant
oxidation
– aerobic 151ff., 187ff., 253, 294
– alcohol 147ff., 204, 249, 407
– aldehyde 353, 407
– alkane 188, 265, 407
– alkene 245
– alkylarene 193, 322
– alkyne 204
– amide 260
– amine 277ff.
– Baeyer-Villiger oxidation of ketone in
fluorinated alcohol solvent 136ff.
– benzylic compound 201
– biocatalytic 179, 306
– biooxidation, see biooxidation
– carbonyl compound 353ff.
– catalytic 117ff., 265
– chemocatalytic 302
– chiral N-hydroxyimide 205
– copper-catalyzed 170
– diol 206f.
– dioxygen 188, 206f., 331
– environmentally benign oxidant 147
– hydroaromatic compound 201
– hydrocarbon 265
– H
2
O
2
176
– ionic liquid 153, 291
– ketone 356
– ketone to lactone and ester 138
– b-lactam 260
– lipophiloselective 345
– liquid phase 315ff.
– metal-free oxidation of aldehyde to carboxylic
acid 354
– metal-mediated 151
– methane 339
– N-methylamine 256
– methylpyridine 199
– methylquinoline 199
– microbial 431
– Mn-catalyzed 371ff., 407
– mono-oxygen donor 317
– organocatalytic 85ff.
– oxoammonium based 147
– oxygen 159, 170ff., 188, 331
– Pd-catalyzed 163
– Pd-bathophenanthroline catalyzed 167
– peroxygen compound 323
– perruthenate-catalyzed 159
– primary amine 259
– primary and secondary alcohol to
aldehyde 159ff.
– Ru-catalyzed 153, 241ff., 260
– RuCl
3
-catalyzed 247ff.
– RuCl
2
(PPh
3
)
3
-catalyzed 260
– Ru(OH)
3
-Al
2
O
3
catalyzed 161
– Ru(TPP)(O)
2
(TPP¼5,10,15,20-
tetraphenylporphyrinato) 264
– secondary amine 258f.
– sulfide 277ff., 294, 410
– tertiary amine 256f., 300ff.
– thiol and thiophenol to disulfide 138
– Ti-catalyzed oxidation 282
oxidative cyanation
– pyrrolidine derivative 257
N-oxide 300
oxidized electron transfer mediator
(ETM
ox
)3
oxirane oxidation 278
oxoammonium based oxidation of
alcohol 147
oxodiperoxomolybdenum(VI) complex 45
a-oxo-ene-diol 249
oxone
Ò
86ff., 135, 279, 306, 324
– derivative 279
oxo-ruthenium complex 263
oxoruthenium(VI) complex 161
oxydehydrogenation 337
– vinylcylohexane 340
– vinylcylohexene 340
oxygen, see also dioxygen 9ff.
– a-oxygen 321
– alkane oxidation 188, 266
– carboxylation of alkane 212
– Cu-catalyzed oxidation 170ff.
– hydroxyacylation 224
– metal-calalyzed oxidation 174
– oxidation 331
– oxidation of alcohol 159ff.
– oxidation of diol 206f.
– oxyalkylation of alkene 222
460
j
Index
– Pd-catalyzed oxidation 163
– Ru catalyzed oxidation 153
– RuCl
3
-catalyzed oxidation 257ff.
– terminal oxidant 293
oxygenation
– anthracene 338
– catechol 264
– Mars–van Krevelen-type 338
– Ru-catalyzed 264
– xanthene 338
N-oxygenation
– N,N-dimethylaniline 428
p
P450, see cytochrome P450
P450
BioI
427
P450
BM3
425ff., 443
P450
cam
439f.
P450
EpoK
426
P450
foxy
425
P450
NikF
426
palladium
– catalyzed oxidation with O
2
163, 206
– giant cluster 163ff.
– nanocluster 168
– Pd(II)-bathophenanthroline-
complex 165ff.
– Pd(II) neocuproin complex 167f.
– PdCl
2
(PhCN)
2
169
– Pd/DMSO system 164
– Pd(OAc)
2
163, 206
– Pd(OAc)
2
[PV
x
Mo
12x
O
40
]
(3þx)
335
– Pd
561
phen
60
(OAc)
180
163
– Pd/pyridine system 164
PEM-MC OsO4 19
4-pentynoic acid 107
peptide
– oxidative modification 261
peptide Schiff-base library 284
peracetic acid 209
peracid 278, 301
perfluoroheptadecan-9-one 135
()-perillyl alcohol 434
peroxidase 298
– V-containing 298
peroxide shunt 438
peroxo complex
– Venturello-type 281
peroxo-cobalt(III) complex 196
peroxo-molybdate 281
peroxo-tungstate 281
1,1
0
-peroxydicyclohexylamine (PDHA) 210f.
peroxygen compound
– oxidation 323
perrhenic acid 134
phase transfer agent 178
phenacetin 435
phenol
– oxidation 262
phenylacetone monooxygenase (PAMO) 360
1-phenylcyclohexene 391
N-phenyl-2-(dicyclohexylphosphanyl)
pyrrole 252
(R)-1-phenylethylamine 64
phenylmethylsulfoxide 322
trans-1-phenyl-3-propyl-4-
chloropiperidine 256
phosphovanadomolybdate 335ff.
photosulfoxidation 215
photosystem II (PSII) 372
phthalimide N-oxyl (PNO) 193ff., 213ff.
– radical 188
b-picoline 200
c-picoline 200
pinane 245
a-pinene 439
(þ)-a-pinene 441
a-pinene oxide 439
piperidine 256
piperidinyloxyl copper(II) complex 173
PIPO (polymerimmobilized piperidinyl
oxyl) 149
pladienolide
– B 100, 432
– D 432
platinum
– asymmetric sulfoxidation 285
– Pt(II) catalyst 357
– Pt(II) complex 77
– Pt(II)methylpyrimidinium-H
5
PV
2
Mo
10
O
40
catalyst 339
PNN (2-(di-t-butylphosphinomethyl)-6-
(diethylaminomethyl)pyridine) 252
polarity reversal catalyst
– NHPI 226
polyene-polyepoxide-polycyclization 107
polyepoxide 107
polyepoxide cyclization 106
polyfluorooxometalate 329
polyketide antitumor macrolide 432
polymer-supported perruthenate (PSP) 158,
254
polymethoxybenzene
– oxidation 264
polyoxometalate (POM) 281, 316ff., 327ff.
– epoxidation 331
– Keggin-type 44, 327
– lanthanide-containing 327
Index
j
461
– lipophiloselective reaction 346
– liquid phase oxidation 315ff.
– Ru-containing 247, 267
– sandwich-type 318ff., 330f.
– sulfoxide complex 323
– V-substituted sandwich type 325
– Wells-Dawson-type 318
polyoxomolybdate 324
– Keggin type 323
– V-substituted 321
polyoxotungstate 189, 329
polyurea microencapsulated OsO4 19
poly(4-vinylpyridine) 63
poly(4-vinylpyridine) N-oxide 63
porphyrin
– catalysis 378
– epoxidation of cis-cyclooctene 48
potassium
– K
2
CO
3
171f.
– K
3
[Fe(CN)
6
] 2ff.
– K
2
[OsO
2
(OH)
4
]2
– K
2
RuO
4
249ff.
pravastatin 432
progesterone 436
L-prolineamide 64
proposed glabrescol 103
propyl 3,3-bis(1-methylimidazol-1-yl)
propionate 67
pyrene 441
pyridazinones 225
pyridine-2,6-bisoxazoline 75
pyridine-2,6-dicarboxylic acid 68ff.
pyridinecarbonitrile 199
pyridinecarboxamide 199
pyridinecarboxylic acid 199
pyridyl ligand 405
pyridylhomothreonine
– hydroxylation 426
pyrrolidine 68
q
Q
3
[PMo
12
O
40
] 281, 322
quinoline 257
quinolinecarboxylic acid 200
8-quinolinol (QOH) 45
r
revised glabrescol 105
rhenium
– compound 133
– epoxidation 52
– [H
0.5
(CH
3
)
0.92
ReO
3
]63
rhenium oxide 61
ring decoration 433
Ritter-type reaction 220f.
– cerium ammonium nitrate (CAN) 220f.
ruthenium
– amide 260
– catalyst 23ff.
– [Cn
Ru(CF
3
CO
2
)
3
(H
2
O)] (Cn
¼N,N
0
,N
00
-
trimethyl-1,4,7-triazacyclononane) 250
– dihydroxylation of a-methylstyrene 24
– dioxoruthenium(IV) complex 243
– epoxidation 74, 243
– K
2
RuO
4
249ff.
– low-valent 245, 266
– mechanism for Ru/TEMPO-catalyzed
oxidation of alcohol 158
– cis-[(Me
3
tacn)-(CF
3
CO
2
)Ru
VI
O
2
]
CF
3
CO
2
26
– Mg
6
Al
2
Ru
0.5
(OH)
16
CO
3
162
– oxidation for organic synthesis 241ff.
– oxidation with O
2
153ff.
– perfluorinated 267
– polyoxometalate 247, 267
– (n-Pr
4
N)(RuO
4
) (TPAP) 249ff.
– Ru
III
(H
2
O)SiW
11
O
39
]
5
320
– Ru-Al-Mg-hydrotalcite 254
– Ru-Al
2
O
3
254
– Ru/AlO(OH) 254
– Ru/benzoquinone system 156
– cis-[Ru(6,6-Cl
2
bpy)
2
(OH
2
)
2
]
2þ
/
t-BuOOH 265
– RuCl
3
with H
2
O
2
249
– RuCl
3
-catalyzed oxidation 247
– [RuCl(dpp)
2
]
þ
265
– RuCl
3
.
3H
2
O/didecyldimethylammonium
bromide 177
– [RuCl(Me
2
SO)(TPA)]
þ
265
– RuCl
2
(PPh
3
)
3
249ff., 260ff.
– RuCl
2
(PPh
3
)
3
-TEMPO 254
– [RuCl
2
(TPA)]
þ
265
– Ru
3
(CO)
12
252
– Ru(CO)
3
(Z
4
-tetracyclone) 251
– Ru-Co-Al-hydrotalcite 254
– Ru-Co-HT 162
– [Ru(p-cymene)Cl
2
]
2
252
– cis-[Ru(dmp)
2
(MeCN)
2
]
2þ
/H
2
O
2
265
– [Ru(dmp)
2
(CH
3
CN)
2
](PF6) (dmp¼2,9-
dimethyl-1,10-phenanthroline) 247
– RuH(PPh
3
)
4
252
– RuHCl(PNN)(CO) (PNN¼2-(di-t-
butylphosphinomethyl)-6-
(diethylaminomethyl)pyridine) 251
– Ru-hydroxyapatite (RuHAP) 254ff.
– cis-[Ru(Me
3
tacn)(O)
2
(CF
3
CO
2
)]
þ
/t-BuOOH
(Me
3
tacn¼N,N
0
,N
00
-1,4,7-trimethyl-1,4,7-
triazacyclononane) 265
462
j
Index