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Smith M.B., March J. — March's Advanced Organic Chemistry: Reactions, Mechanisms, and Structure |
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Предметный указатель |
-Chloro-5-cholesten- 146
-Cholestanol 1512
-Friedelanol 1395
-Cholest-14-en- 1512
nomenclature, IUPAC for mechanisms 385
nomenclature, IUPAC for mechanisms 384
1 mechanism, and ester hydrolysis 473
2 mechanism, and ester hydrolysis 473
mechanism, and ester hydrolysis 473
mechanism, and ester hydrolysis 473
-dppp, reduction of allyl amines 1559
nomenclature, IUPAC for mechanisms 385
nomenclature, IUPAC for mechanisms 384
values 454
and pH 335
also see “Acidity constant”
see “Nitrogen dioxide”
see “Acidity constant”
hybridization, and radicals 244
hybridization, and carbanions 233
see “Substitution”
mechanism 763—766
mechanism and caiboxylate ion decarboxylation 733
mechanism and electrophilic aromatic substitution 681
see “Substitution”
mechanisms 759—763
mechanism 760
see “Substitution”
mechanism 759—763
see “Substitution
see “Substitution
see “Substitution
see “Substitution
reactions see “Substitution
see “Substitution
see “Substitution
see “Substitution
see “Substitution”
mechanism see “Substitution
-Bromoacetophenone 436
-Chloroacetophenone 436
-Dithiomethyleneketones 1229
-Hydroxy ketones by acyloin condensation 1562
-Hydroxy ketones from esters 1562
-Lactams, formation from chloro amides 514
-Methoxyvinyllithium 1227
nomenclature, for steroids 146
-Carotene 1236
-Lactams from aminocyclopropanols 1417
-Lactams from enamines and isocyanates 1250
-Lactams from imines and ketenes 1250
-Lactones hydrolysis mechanism 473
-Lactones reaction with ammonia 511
-Thiolactams, from thioketones and imines 1250
-Lactones, hydrolysis mechanism 473
-Oximinocarboxylic ester, from cyclic ketones 1522
-Allyl complex mechanism 772
-Bond, and carbanion stability 232
values, and elimination reactions 1313 1321
values 369—370 372
-bond rearrangements 1459—1460 1465
-substitution, mechanism 702
1,1,1-Trifluoroethanol, as a solvent 451
1,1,1-Trihalides, hydrolysis of 463
1,1,2,2-Tetrabromoethane 170
1,1,2,2-Tetrachloroethane 170
1,1,2,2-Tetrafluoroethane 170
1,1,4,4-Tetramethyl-7-cyclodecyltri-methylammonium chloride 1304
1,1,4,4-Tetramethylcyclodecyl bromide 1306
1,1-Dichloroethene, reaction with ethoxide 428
1,1-Dicyclopropylethene 1443
1,1-Diethoxyethane, hydrolysis of 466
1,1-Diphenylethanediol 1384
1,2,3-Cyclohexanetriol, and meso compound 161
1,2,3-tri-t-butylcyclobutadiene, valence tautomerism 1449
1,2,3-Trioxolane, from ozonolysis of alkenes 1523
1,2,4-tri-t-butylbenzene 1433
1,2,4-Trioxolane see “Ozonide”
1,2-Diamines, from dimerization of iraines 1561
1,2-Dibromoethane, dipole moment 16
1,2-Dicarbonyl compounds from 1,3-dithianes 1664
1,2-Dicarbonyl compounds from acyl halides 1664
1,2-Dicarbonyl compounds from alkenes 1665
1,2-Dicarbonyl compounds from alkyl halides 1664
1,2-Dicarbonyl compounds from alkynes 1665
1,2-Dicarbonyl compounds from aromatic compounds 1665
1,2-Dicarbonyl compounds from carbon dioxide 1665
1,2-Dicarbonyl compounds from esters 1664
1,2-Dicarbonyl compounds from imines 1665
1,2-Dicarbonyl compounds from organolithium reagents 1664
1,2-Dicarbonyl compounds from oxidative cleavage of -amino ketones 1665
1,2-Dicarbonyl compounds fromketones 1665
1,2-Dichloroethene, reaction with ethoxide 430
1,2-difluoroethane 170
1,2-Dimethoxyethane 236
1,2-Dimethylcyclohexene, reaction with bromine 974
1,2-Diols conversion to cyclic sulfates 462
1,2-Diols from alcohols 1667
1,2-Diols from aldehydes 1667
1,2-Diols from aromatic aldehydes 1667
1,2-Diols from hydrolysis of epoxides 1667
1,2-Diols from ketones 1667
1,2-Diols fromalkenes 1048—1051 1667
1,2-Hydride shifts 1387
1,3,4-tri-t-Butylbenzene 189
1,3,5,7-Octatetraene 1433
1,3,5-Trienes, and Cope rearrangement 1445
1,3-Dicarbonyl compounds by Michael addition 1665
1,3-Dicarbonyl compounds by the Blaise reaction 1665
1,3-Dicarbonyl compounds by the Claisen condensation 1665
1,3-Dicarbonyl compounds by the Dieckmann condensation 1665
1,3-Dicarbonyl compounds by the Knoevenagel condensation 1665
1,3-Dicarbonyl compounds by the Stork enamine synthesis 1665
1,3-Dicarbonyl compounds from -halo esters 1665
1,3-Dicarbonyl compounds from -keto esters 1665
1,3-Dicarbonyl compounds from acetals 1665
1,3-Dicarbonyl compounds from active hydrogen compounds 1665
1,3-Dicarbonyl compounds from aldehydes 1665
1,3-Dicarbonyl compounds from alkenes 1665
1,3-Dicarbonyl compounds from aromatic compounds 1665
1,3-Dicarbonyl compounds from carboxylic acid salts 1665
1,3-Dicarbonyl compounds from diethyl oxomalonate 1665
1,3-Dicarbonyl compounds from enamines 1665
1,3-Dicarbonyl compounds from esters 1665
1,3-Dicarbonyl compounds from ethyl diazoacetate 1665
1,3-Dicarbonyl compounds from ketals 1665
1,3-Dicarbonyl compounds from ketones 1665
1,3-Dicarbonyl compounds from nitrites 1665
1,3-Dicarbonyl compounds from rearrangement of epoxy ketones 1665
1,3-Dichlorobutane, an ambident substrate 461
1,3-Diols by the Prins reaction 1667
1,3-Diols by the Tollens reaction 1667
1,3-Diols from aldehydes 1667
1,3-Diols from alkenes 1667
1,3-Dipolar additions see “Cycloadditions [3+2]”
1,3-Dipoles azides 1060
1,3-Dipoles azomethine imines 1060
1,3-Dipoles azomethine ylids 1060
1,3-Dipoles azoxy compounds 1060
1,3-Dipoles carbonyl oxides 1060
1,3-Dipoles diazoalkanes 1060
1,3-Dipoles nitrile imines 1060
1,3-Dipoles nitrile oxides 1060
1,3-Dipoles nitrile ylids 1060
1,3-Dipoles nitrones 1060
1,3-Dipoles nitrous oxide 1060
1,3-Dipoles ozone 1060
1,3-Dipoles thiocarbonyl ylids 1061
1,3-Hydride shifts 1387
1,3-Pentanedione, 347
| 1,4-Cycloheptadiene 1447
1,4-Diazabicyclo[2.2.2]octane see “DABCO”
1,4-Dicarbonyl componnds from alkynes 1665
1,4-Dicarbonyl componnds from aromatic compounds 1665
1,4-Dicarbonyl componnds from carboxylic acids 1665
1,4-Dicarbonyl componnds from cleavage of furans 1665
1,4-Dicarbonyl componnds from enolate anions 1665
1,4-Dicarbonyl componnds from esters 1665
1,4-Dicarbonyl componnds from ketones 1665
1,4-Dicarbonyl componnds from silyl enol ethers 1665
1,4-Dicarbonyl componnds from succinic anhydride 1665
1,4-Dicarbonyl componnds from unsaturated ketones 1665
1,4-Dienes and di--methane rearrangements 1460
1,4-Dienes photolysis of 1460
1,4-Dienes-addition reactions 980
1,4-Diketones from coupling of enolate anions 1543
1,4-Diketones from silyl enol ethers 1543
1,4-Diketones hydrolysis of 1181
1,4-Elimination 1326
1,4-ketones, from alkynes and organolithium reagents 1033
1,4-Pentadiene, resonance energy 37
1,4’-Diaminobiphenyl 1456
1,5,9-Cyclododecatriene 1091
1,5-Cyclooctadiene 1091
1,5-Dicarbonyl compounds from esters 1665
1,5-Dicarbonyl compounds from silyl enol ethers 1665
1,5-Dicarbonyl compounds from silyl ketene acetals 1665
1,5-Dicarbonyl compounds from unsaturated ketones 1665
1,5-Dienes by Cope rearrangement 1444—1449
1,5-Dienes from 1,5-dienes 1444—1449
1,5-Diynes, Cope rearrangement 1445
1,5-heptadiene 1444
1,5-hexadiene, by Hofmann elimination 1331
1,6-Hexanediol 480
1,8-Diazabicyclo[5.4.0]undecene see “DBU”
1-Bromo- 1,2-dichloroethene 157
1-Chlorocyclopropene, pyrolysis of 1400
1-Chloroethene, bonding 38
1-Chloroethyne, reaction with arylthio anions 430
1-Decene, double bond migration 772
1-Methyl-2-chloropyridinium iodide 1327
1-Phenyl-2-propanol 391
1-Trishomobarrelyl cation 224—225
13(18)-oleanene 1395
18-Dicyclohexanocrown-6 455
2,2,2-Trichloroacetimidate, in esterification reactions 486
2,2,2-Trifluoroethanesulfonate, leaving group 446
2,2,3-Trimethyl-2-butyl cation 419
2,2’-Hydrazonaphthalene 1456
2,3,5,6-Tetrachloro-l,4-benzoquinone 1511
2,3-Diarylthiiren-1,1-dioxides 1343
2,3-Dibromobutane, and E2 elimination 1301
2,3-Dichloro-5,6-dicyano-l,4-benzoquinone see “DDQ”
2,4,6-Trimethylbenzoic acid see “Mesitoic acid”
2,4-Pentanedione, and hydrogen bonding 99—100
2,4-tri-t-butylbenzene 189
2,5-Dihydrothiophene-1,1-dioxide 1342
2,7-Dihydrothiepin-1,1-dioxide 1342
2-Bromopentane, Zaitsev elimination 1318
2-Bromopropane, bond angles 21
2-Buten-l-ol, reaction with 422
2-Cyclopropylpropyl cation 225
2-Ethyltetrahydrofuran 480
2-Fluoroethanol 170
2-Methylpiperidine, and Hofmann elimination 1331
2-Methytaaphthalene electrophilic aromatic substitution 689
2-Methytaaphthalene oxidation of 1527
2-Naphthoic acid, from 2-methylnaphthalene 1527
2-Naphthol, excited states 311
2-Norborneol 162
2-Octyl brosylate 398—400
2-Octyl iodide, reaction with radiolabeled iodide 392
2-Phenylpropyl cation 225
2-Propanone see “Acetone”
2-Trimethylsilylmethyl-2-propen-l -yl acetate 1076
2-Vinylcyclobutanols, rearrangement 1444
3,3,7,7-Tetramethylcycloheptyne 187
3,3-Dimethyl-l-butyl cation 1387
3,3-Dimethylpentanal 1390
3,4-Dimethoxydiphenylmethyl acetate 396
3,5-Dimethylcyclohexanol 161
3-Bromo-2-butanol, reaction with HBr 405 411
3-Buten-2-ol, reaction with 422
3-Ethylpiperidine 1634
3-Hexyne, trimerization of 1090
3-Hydroxypropanoic acid 333
3-Methyl-l,5-hexadiene 1444
3-Methylene-l,4-pentadiene, bonding orbitals 39
3-Pentanone, reaction with ethyl diazoacetate 1408
4,4-Diphenyloxathiolan-5-ones 1355
4,N,N-Dimethylaminopyridine (DMAP) 483 1340
4-Vinylcyclohexene 1447
7-Methyl-2-norcamphor 163
9-BBN 1013
9-BBN B — alkyl derivatives, with CO and reducing agents 1424
9-BBN reaction of enamines 530 1014
9-BBN reduction of conjugated carbonyl compounds 1200
9-Borabicyclo[3.3.1]nonane see “9-BBN”
9-Perchlorofluorenespirocyclohex-2',5'-diene 44
A nomenclature, IUPAC for mechanisms 384
A-values, table 174
ab initio studies 34 36
ab initio studies, reaction 393
ab initio studies, 1,2 alkyl shifts, electrophilic 1392
ab initio studies, acids and bases 339
ab initio studies, and enolate anions 237
ab initio studies, and nitrenes 253
ab initio studies, and the Mills-Nixon effect 690
ab initio studies, and the norbornyl cation 415
ab initio studies, cubyl cation and the SnI reaction 397
ab initio studies, electrophilic addition to cyclopropanes 990
ab initio studies, MO, of bromonium ion 973
ab initio studies, nucleophilic addition to carbonyls 1173
ab initio studies, transition state structures for radicals 900
ab initio, acid strength calculation 328
Absolute configuration 138—143
Absolute configuration, and diastereomers 146
Absolute configuration, and glyceraldehyde 138
Absolute configuration, and Mosher's derivatives 142—143
Absolute configuration, and radicals substitution 899
Absolute configuration, and the reactions 761
Absolute configuration, and the CIP system 139—141
Absolute configuration, and x-ray 142
Absolute configuration, by derivatization 142—143
Absolute configuration, determination of 141—143
Absolute configuration, insertion reactions of carbenes 790
Absolute hardness 341
Absorption and photochemistry 308
Absorption differential, and resolution 152
Abstraction and radicals 896
Abstraction hydride, photochemical 1513
Abstraction hydrogen, radical, and the Hammett equation 903
Abstraction of nitrenes 254
Abstraction radical, rate of reaction 901
Acenaphthylene, reaction with DBr 975
Acetals and enol ether formation 1181
Acetals and the Mukaiyama aldol reaction 1223
Acetals by the Prins reaction 1642
Acetals by transacetalation 1181
Acetals by transetherification 480 1642
Acetals elimination reactions 1329
Acetals from -halo ethers 1642
Acetals from alcohols 997 1180 1642
Acetals from aldehydes 1180 1642
Acetals from alkenes 1642
Acetals from alkoxides 477 1642
Acetals from alkynes 997 1642
Acetals from cyclization of -hydroxy ethers 1642
Acetals from dihalides 477 1642
Acetals from Grignard reagents 1642
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