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Francis A. Carey, Richard J. Sundberg
Advanced Organic Chemistry. Part B
Part B: Reaction and Synthesis
5. Auflage, 1322 Seiten, 3968 illus., 4 in color, 27 tab., Gebunden
Springer-Verlag GmbH | ISBN: 038768350x
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PrefaceThe methods of organic synthesis have continued to advance rapidly and we have made an effort to reflect those advances in this Fifth Edition. Among the broad areas that have seen major developments are enantioselective reactions and transition metal catalysis, Computational chemistry is having an expanding impact on synthetic chemistry by evaluating the energy profiles of mechanisms and providing structural representation ot unobservable intermediates and transition states. The organizat...
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Advanced Organic Chemistry Part B: Reactions and Synthesis Fifth Edition Francis A. Carey and Richard J. Sundberg Since its original appearance in 1977, Advanced Organic Chemistry has maintained its place as the premier textbook in the field, offering broad coverage of the structure, reactivity, and synthesis of organic compounds. As in the earlier editions, the text contains extensive references to both the primary and review literature and provides examples of... [weiter lesen] |
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Francis A. Carey Department of Chemistry University of Virginia Charlottesville, VA 22904 Richard J. Sundberg Department of Chemistry University of Virginia Charlottesville, VA 22904 Advanced Organic Chemistry, Part B, examines the major reactions that are applied in synthesis. It provides information on reagents, mechanism, and stereochemistry. The Schemes provide specific examples. Together with Part A, Structure and Mechanisms, the two volumes are intended to provide advanced undergradu... [weiter lesen] |
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Index
AAcetals as electrophiles in allyl silane addition, 820-821
- Mukaiyama aldol reaction, 85-86
- protective groups for alcohols, 258-262
- carbonyl compounds, 272-275
- diols, 266-267
Acrylic acid derivatives α -amido, hydrogénation of computational model for...
- enantioselective, 380, 384
- enantioselective hydrogenation, 380
- examples, 385-386
Acyl anion equivalents, 1167-1169
Acyl chlorides α -halogenation, 331
- reaction with organocadmium compounds, 661-662
- organomagnesium compounds, 637-638
- organozinc compounds, 661
- silanes, 828-829
- synthesis using oxalyl chloride, 243
- triphenylphosphine, carbon tetrachloride, 244
Acyl iminium ions, 145-146, 199, 828-829
Acylation of alcohols, 243-252
- by acyl halides, 244
- by acyl imidazolides, 246-247
- by pyridine-2-thiol esters, 248
- catalysis by DMAP, 244
- Lewis acid catalysts for, 245-246
- using 3-chloroisoxazolium salts, 247
- using 2-chloropyridinium salts, 247
- using DCCI, 247
alkenes, 881-883
- intramolecular, 882-883
amines, 252-257
- carbon nucleophiles, 148-149
- enolates, 150-157
- ester condensation, 149-157
- malonate magnesium salts, 152
- silanes, ketones from, 828-829
Acylium ions
- in Friedel-Crafts reaction, 1019
- reaction with alkenes, 881-883
Acyloin condensation, 450
- mechanism, 450
Alcohols acylation of, 243-252
- by acyl halides, 246
- by acyl imidazolides, 246-247
- by Fischer esterification, 252
- by pyridine-2-thiol estes, 248
- catalysis by DMAP, 244
- Lewis acid catalysts for, 242
- using 3-chloroisoxazolium salts, 247
- using 2-chloropyridinium salts, 247
- using DCCI, 247
allylic epoxidation of, 1082-1088
- synthesis from aldehydes and allylic boron
- compounds, 797-809
- from aldehydes and allylic silanes, 815-830
- from alkenes and selenium dioixide, 1124-1126- from alkenes and singlet oxygen, 111...
Alcohols (Com.)
- from sulfoxides by [2, 3]-sigmatropic
- rearrangement, 581
- by wittig reaction, 162
- ß-amino, from epoxides, 1107
- ß-azido, from epoxides, 1107
- conversion to halides, 217-223
- examples, 221
- triphenylphosphine as co-reagent in, 219-221
- conversion to ethers, 227
- converson to sulfonate esters, 216
- ß-cyano, from epoxides, 1106-1107
- enantioselective synthesis
- by hydroboration-oxidation, 351
- by reduction of ketones, 415-422
- inversion of configuration by Mitsunobu reaction, 228
- oxidation 1063-1074
- chromium dioxide, 1068
- chromium (VI) reagents, 1063-1069
- Dess-Martin reagent, 1072-1073
- dimethyl sulfoxide, 1070-1072
- manganese dioxide, 1067-1068, 1069
- oxoammonium ions, 1074
- potassium ferrate, 1068
- Swern, 1070
- protective groups for, 258-267
acetals as, 258-262
allyl, 264
allyloxycarbonyl, 267
- benzyl, 262-263
- t-butyl, 262
- t-butyldimethylsilyl, 264
- dimethoxybenzyl, 263
- 2, 4-dimethoxytriphenylmethyl, 262
- ethers as, 262-264
- 1-ethoxyethyl, 260- 2-methoxyethoxymethyl, 260- 2-methoxypropyl, 259-260
- methoxymethyl, 260
- p-methoxyphenyl, 263
- p-methoxytrimphenylmethyl, 262
- methylthiomethyl, 260
- table of, 267
- tetrahydropyranyl, 260
- trichloroethyloxycarbonyl, 265
- triisopropylsilyl, 264-265
- trimethylsilyl, 264
- 2-trimethylsilylethoxymethyl, 261
- triphenylmethyl, 262
- triphenylsilyl, 265
- reductive deoxygenation via thiono esters, 433
- examples, 434
- synthesis from
aldehydes and organometallic reagents, 638
alkenes by hydroboration-oxidation, 344-347, 351
alkenes by oxymercuration-reduction, 294-298
- boranes by carbonylation, 786-787
- epoxides by reduction, 1109-1110
- esters and organomagnesium compounds, 637
- ketones and organometallic reagents, 638
- ketones by reduction, 407-422
- unsaturated
- halocyclization of, 317-318
Aldehydes aldol reactions of, 65-78
aromatic
- reduction by silanes, 425
- synthesis by formylation, 1024
- enolates, alkylation of, 31
- oxidation
- manganese dioxide, 1132
- reactions with
alkynyl boranes, 805
allylic boron compounds, 797-809
allylic silanes, 815-827
allenyl tin compounds, 850-851
allylic tin compounds, 834-849
- organomagnesium compounds, 638
- organozinc reagents, 653-654
- silanes from, 836
- stereoselectivity of,
- in aldol reactions, 86-101
- synthesis from alcohols by oxidation, 1063-1073
alkenes by hydroformylation, 759-760
- boranes by carbonylation, 786-787- formamides and organomagnesium reagents, 638
- nitriles by partial reduction, 402-403
- esters, by partial reduction, 401-403
- N-methoxy-N-methylamides, 402
- triethyl orthoformate and organomagnesium reagents, 638-639
Alder rule, 478
Aldol reaction
- of N-acylthiazoline-2-thiones, 81
- boron enolates in, 71-73
- chiral, 117-119
- chiral auxiliaries for, 114-119
- chiral catalysts for, 125-133
- cyclic transition structure for, 67-68
- directed 65-67
- examples, 66
- double Stereodifferentiation in, 108-114
- examples, 111-114
- enantioselective catalysts for, 125-133
- examples, 133
- enolate equivalents in, 65, 82-86
- ester enolates in, 78-81
- generalized 64-65
- intramolecular, 134-139
- examples, 135-136
- in longifolene sysnthesis, 1189
- Robinson annulation as, 134-139
- ketone enolates in 67-69
- stereoselectivity of, 68-69
- kinetic versus thermodynamic control, 64-65, 71
- macrocyclization by in epothilone A synthesis, 1224
- mechanism, 64-65
- Mukaiyama aldol reaction, 82-86
- stereoselectivity of, 65-78, 93-101
- polar substituent effects in, 97, 105
- stereoselectivity of, 86-134
- chelation effects in, 92-96, 102-105
- control by ajdehyde, 87-101
- control by enolate, 101-108
- Felkin model for, 90
Alkenes
addition of trifluoroacetic acid, 294
addition reactions with hydrogen halides, 290-293
- carbocation rearrangements during, 291
- stereochemistry of, 291-293
allylic oxidation, 1116-1126
- chromium reagents, 1116-1117
arylation
- Meerwein arylation, 1035
- palladium-catalyzed, 715-720
aziridination of, 947
- carboalumination, 354-355
- [2+2]cycloaddition
- examples, 543
- intramolecular, 540-541
- photocycloadditions, 544-548
- with carbonyl compounds, 548-551
- with ketenes, 539-542
- dihydroxylation, 1074-1081
- computational model for, 1078-1079
- co-oxidants for, 1076
- enantioselective. 1076-1078
- examples. 1080
- diimide, reduction by, 388-390
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