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Carey F.A., Sundberg R.J. — Advanced organic chemistry (Part B)
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Íàçâàíèå: Advanced organic chemistry (Part B)
Àâòîðû: Carey F.A., Sundberg R.J.
Àííîòàöèÿ: Since its original appearance in 1977, Advanced Organic Chemistry has found wide use as a text providing broad coverage of the structure, reactivity and synthesis of organic compounds. The Fourth Edition provides updated material but continues the essential elements of the previous edition. The material in Part A is organized on the basis of fundamental structural topics such as structure, stereochemistry, conformation and aromaticity and basic mechanistic types, including nucleophilic substitution, addition reactions, carbonyl chemistry, aromatic substitution and free radical reactions. The material in Part B is organized on the basis of reaction type with emphasis on reactions of importance in laboratory synthesis. As in the earlier editions, the text contains extensive references to both the primary and review literature and provides examples of data and reactions that illustrate and document the generalizations. While the text assumes completion of an introductory course in organic chemistry, it reviews the fundamental concepts for each topic that is discussed. The Fourth Edition updates certain topics that have advanced rapidly in the decade since the Third Edition was published, including computational chemistry, structural manifestations of aromaticity, enantioselective reactions and lanthanide catalysis. The two parts stand alone, although there is considerable cross-referencing. Part A emphasizes quantitative and qualitative description of structural effects on reactivity and mechanism. Part B emphasizes the most general and useful synthetic reactions. The focus is on the core of organic chemistry, but the information provided forms the foundation for future study and research in medicinal and pharmaceutical chemistry, biological chemistry and physical properties of organic compounds.
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Ðóáðèêà: Õèìèÿ /
Ñòàòóñ ïðåäìåòíîãî óêàçàòåëÿ: Ãîòîâ óêàçàòåëü ñ íîìåðàìè ñòðàíèö
ed2k: ed2k stats
Èçäàíèå: 4th edition
Ãîä èçäàíèÿ: 1938
Êîëè÷åñòâî ñòðàíèö: 965
Äîáàâëåíà â êàòàëîã: 16.04.2006
Îïåðàöèè: Ïîëîæèòü íà ïîëêó |
Ñêîïèðîâàòü ññûëêó äëÿ ôîðóìà | Ñêîïèðîâàòü ID
Ïðåäìåòíûé óêàçàòåëü
Diazo compounds, reactions with ketones 608—609
Diazoketones see “Ketones diazo”
Diazomethane, in preparation of methyl esters 152—153
Diazomethane, in ring expansion of ketones 608—609
Diazonium ions, aromatic 714—722
Diazonium ions, aromatic, conversion to aryl azides 721
Diazonium ions, aromatic, conversion to aryl halides 719—721
Diazonium ions, aromatic, phenols from 717
Diazonium ions, aromatic, preparation of 714—715
Diazonium ions, aromatic, radicals from 731
Diazonium ions, aromatic, reaction with thiolates 715 721
Diazonium ions, aromatic, reductive dediazonation of 716—717
Diazonium ions, as intermediates in ketone ring expansion 608
Diborane, addition to alkenes 226—228
Diborane, as reducing agent 267 270—271
Diborane, as reducing agent, amides 270—271
Diborane, as reducing agent, carboxylic acids 270
Diborane, as reducing agent, epoxides 778
Dicyanodichloroquinone, oxidative removal of protecting groups 826
Dicyclohexylcarbodiimide, activation of carboxylic acids by 169 172—177 830 899
Dieckmann condensation 103
Diels — Alder reaction 332—359
Diels — Alder reaction, asymmetric 349—353
Diels — Alder reaction, catalysis by Lewis acids 336—338 349
Diels — Alder reaction, enantioselective 353—353 357
Diels — Alder reaction, frontier orbitals in 332—335
Diels — Alder reaction, intramolecular 353—359 404 883
Diels — Alder reaction, inverse electron demand 333 407
Diels — Alder reaction, of cyclopentadienones 405
Diels — Alder reaction, of pyridazines 407
Diels — Alder reaction, of pyrones 348 883 885
Diels — Alder reaction, of quinodimethanes 345—347
Diels — Alder reaction, of triazines 407
Diels — Alder reaction, regioselectivity of 333—334
Diels — Alder reaction, stereoselectivity 334
Diels — Alder reaction, transition state of 335
Dienes, Diels — Alder reactions of 345—348
Dienes, intramolecular photocycloaddition of 369
Dienes, preparation from, 2,5-dihydrothiophene-l,l-dioxides 404
Dienes, preparation from, alkenyl halides and alkenyl boranes 520
Dienes, preparation from, alkenyl halides and alkenyl Grignard reagents 508
Dienes, preparation from, alkenyl halides by nickel-catalyzed coupling 527
Dienes, reaction with singlet oxygen 786
Dienophiles 339—344
Dienophiles, as synthetic equivalent groups 340—343
Dienophiles, benzyne as 727
Dienophiles, masked functionality in 340—343
Diethylaluminum cyanide 46
Diimide, generation and reduction by 262
Diisobutylaluminum hydride for reduction of, amides 269
Diisobutylaluminum hydride for reduction of, esters and lactones 268
Diisobutylaluminum hydride for reduction of, nitrites 269
Diisobutylaluminum hydride for reduction of, unsaturated ketones 272
Dimethyl sulfide, chlorination in oxidation of alcohols 754—755
Dimethyl sulfoxide, as polar aprotic solvent 3 21—22 27 149 203 280 408
Dimethyl sulfoxide, in conversion of alkenes to bromohydrins 203
Dimethyl sulfoxide, in oxidation of alcohols 752—755
Dimethyl sulfoxide, in Pummerer reaction 824
Dimethylboron bromide, cleavage of ethers by 159—163
Dimethylformamide, as hydrogen atom donor 716
Dimethylformamide, as solvent 21—22 27 149 280 728
Dimethylpropyleneurea, solvation by 389 438
Dimethylsulfonium methylide 122—126
Dimethylsulfoxonium methylide 122—126
Dioxanes, alkenyl as dienophiles 350
Dioxetanes 784—785
Dioxiranes, as oxidants 771—772 893
Dioxolanes, alkenyl, as dienophiles 343—344 350
Dioxolanes, as carbonyl-protecting groups 835—836
Dioxolanes, reactions with allylic silanes 572—573
Diphenylphosphoryl azide, activation of carboxylic acids by 176—177
Dipolar cycloaddition reactions 359—367
Dipolar cycloaddition reactions, enantioselective 365
Dipolar cycloaddition reactions, intramolecular 364—365
Dipolar cycloaddition reactions, regioselectivity in 360—361
Dipolar cycloaddition reactions, stereoselectivity in 360—361
Dipolarophiles 359
Dithianes, as acyl anion equivalent 840 856
Dithianes, lithiation of 840
Dithioketals, as carbonyl protecting groups 836—838 862
DMF see “Dirnethylformamide”
DMPU see “Dimethylpropyleneurea”
DMSO see “Dimethyl sulfoxide”
Double stereodifferentiation 83—84 872
Electrophilic aromatic substitution 693—714
Elimination reactions, carbenes from - 623—625
Elimination reactions, cheletropic 403—404
Elimination reactions, of -hydroxysilanes 120—121
Elimination reactions, of diazenes 403
Elimination reactions, thermal 408—414
Enammes, alkylation of 1 31—34
Enammes, conjugate addition to enones 46—47
Enammes, cycloaddition with nitrogen heterocycles 407
Enammes, halogenation of 219
Enammes, nucleophilicity 32
Enammes, of cyclohexanone 33
Enammes, photochemical cycloaddition 376
Enammes, preparation of 31—32
Enammes, [2 + 2] cycloaddition reactions of 370
Enantioselective catalysts in, aldol addition reactions 88—90
Enantioselective catalysts in, alkylzinc addition to aldehydes 461
Enantioselective catalysts in, allylic oxidation of alkenes 804
Enantioselective catalysts in, carbene insertion reactions 637
Enantioselective catalysts in, conjugate addition reactions of organometallic reagents to enones 494
Enantioselective catalysts in, Diels — Alder reactions 350—355
Enantioselective catalysts in, dihydroxylation of alkenes 759—760
Enantioselective catalysts in, dipolar cycloaddition reactions 365
Enantioselective catalysts in, ene reactions 401
Enantioselective catalysts in, epoxidation 762—766 772
Enantioselective catalysts in, palladium-catalyzed alkylation of malonate esters 502
Enantioselective catalysts in, Robinson annulation 95
Enantioselective reactions, addition of allylic boranes to aldehydes 561—563
Enantioselective reactions, addition of organocopper reagents to enones 491—494
Enantioselective reactions, addition of organozinc reagents to aldehydes 461
Enantioselective reactions, aldol additions of N-acyl oxazolidinones 85—87
Enantioselective reactions, aldol condensations involving double stereodifferentiation 83—89
Enantioselective reactions, alkylation of alkynes by organoboranes 556—559
Enantioselective reactions, alkylation of hydrazones 36—37
Enantioselective reactions, alkylation of N-acyl oxazolidinones 30—31
Enantioselective reactions, alkylation of oxazolines 38—39
Enantioselective reactions, Cope rearrangement of 1,5-dienes 379—380
Enantioselective reactions, Diels — Alder additions 349—353
Enantioselective reactions, epoxidation of allylic alcohols 762—764
Enantioselective reactions, hydroboration 230 236—238
Enantioselective reactions, hydrogenation 253—259
Enantioselective reactions, in synthesis of longifolene 876
Enantioselective reactions, ketones from organoboranes 553—554
Enantioselective reactions, Robinson annulation reaction 95
Ene reaction 399—403
Enol ethers, Diels — Alder reactions with nitrogen heterocycles 408
Enol ethers, lithiation of 840
Enol ethers, of -diketones, reduction to enones 273
Enol ethers, oxidation by lead tetraacetate 796
Enol ethers, oxidation by singlet oxygen 784—785
Enol ethers, photochemical cycloaddition 376
Enol ethers, preparation from esters by Lombardo's reagent 462
Enol ethers, regioselectivity in Heck reaction 505
Enol phosphate esters, nickel-catalyzed coupling with Grignard reagents 529
Enol phosphate esters, reduction of 296
Enol silyl ethers see “Silyl enol ethers”
Enol sulfonate esters 309 515 885
Enolates, acylation of 101—110
Enolates, alkylation of 1 11—20
Enolates, alkylation of, by conjugate addition 39—44
Enolates, alkylation of, intramolecular 26
Enolates, alkylation of, O- versus C- 23—28
Enolates, arylation by palladium catalyzed substitution 510
Enolates, boron, aldol addition reactions of 71—74 86—88
Enolates, boron, formation from ketones 71—72
Enolates, carboxylation of 108
Enolates, formation of 1—11
Enolates, formation of, by reduction of -enones 11 292—293
Enolates, formation of, enantioselective 8—9
Enolates, formation of, from -unsaturated ketones 9—10
Enolates, formation of, from enol acetates 10
Enolates, formation of, from trimethylsilyl enol ethers 10—11
Enolates, formation of, in competition with Grignard addition 447
Enolates, formation of, kinetic versus thermodynamic control of 5—8
Enolates, formation of, regioselectivity of 5—8
Enolates, formation of, stereoselectivity of 8—9 65—66
Enolates, halogenation of 219
Enolates, in aromatic substitution reactions 734—735
Enolates, in Robinson annulation reaction 89—95
Enolates, magnesium, acylation of 105—108
Enolates, of -unsaturated ketones, alkylation 27
Enolates, of -unsaturated ketones, protonation of 27
Enolates, of cyclohexanones, stereoselective alkylation 17—18
Enolates, of decalones, stereoselective alkylation 18—19
Enolates, of esters, acylation of 101—108
Enolates, of esters, stereoselective formation 389
Enolates, of isopropyl phenyl ketone, O- versus C-alkylation 25
Enolates, of N-acyl oxazolidinones, aldol addition reactions 75 85—86
Enolates, of N-acyl oxazolidinones, enantioselective alkylation 30—31
Enolates, oxidation by, -pyridine-HMPA 798
Enolates, oxidation by, molecular oxygen 800—802
Enolates, oxidation by, sulfonyloxaziridines 797—798
Enolates, reactions with, benzene-chromium tricarbonyl complex 534—535
Enolates, reactivity, effect of, counter ion 23
Enolates, reactivity, effect of, crown ethers 23
Enolates, reactivity, effect of, hexamethylphoshoric triamide 23
Enolates, reactivity, effect of, solvents 21—23
Enolates, reactivity, effect of, tetramethylethylenediamine 23
Enolates, selenenylation of 220
Enolates, structures of 24
Enolates, sulfenylation of 220
Enolates, tin 76—77 89
Enolates, titanium 74—75
Enolates, zirconium 77
Enols, in aldol condensations 57—60
Enols, in halogenation of ketones 216—220
Epothilone A, synthesis 890—896
Epoxides, preparation from, -halo esters 127
Epoxides, preparation from, alkenes by epoxidation 767—772
Epoxides, preparation from, allylic alcohols by epoxidation 762—764 772
Epoxides, preparation from, amines 775 903
Epoxides, preparation from, azide ion 776
Epoxides, preparation from, carbonyl compounds and sulfur ylides 125—126
Epoxides, preparation from, cyanide ion 776
Epoxides, preparation from, diethylaluminum cyanide 776
Epoxides, preparation from, hydrogen bromide 775
Epoxides, preparation from, organocopper reagents 487
Epoxides, preparation from, organolithium compounds 454
Epoxides, preparation from, selenide ions 781
Epoxides, rearrangement to carbonyl compounds 778—779
Epoxides, reduction to alcohols 284 776—778 878
Epoxides, ring-opening reactions 772—778
Epoxides, trimethylsilyl, preparation of 127
Esters, -alkoxy, aldol addition of enolates 68—70
Esters, -alkoxy, Claisen rearrangement of silyl enol ethers 389—391
Esters, -alkoxy, enolates of 391
Esters, -diazo, reaction with organoboranes 556
Esters, -diazo, rhodium-catalyzed carbenoid reactions of 636—637
Esters, -unsaturated, addition of organocopper reagents to 489
Esters, -unsaturated, copper-catalyzed addition of Grignard reagents 494—495
Esters, -unsaturated, preparation by palladium-catalyzed carbonylation 521
Esters, -unsaturated, reaction with allylic silanes 576
Esters, -unsaturated, reduction of 272
Esters, -keto, alkylation of 11—14 23—25 41
Esters, -keto, reaction with -allylpalladium compounds 501
Esters, -keto, synthesis by enolate acylation 101—109
Esters, -sulfonyl, reaction with -allylpalladium compounds 502—503
Esters, acetylenic, addition of organocopper reagents to 493
Esters, as alcohol-protecting groups 829—831
Esters, condensation reactions of 101—105
Esters, conversion to, amides 177
Esters, conversion to, enol ethers by Lombardo's reagent 462
Esters, enantioselective synthesis of 30—31
Esters, enolates of, acylation 101—108
Esters, enolates of, aldol addition reactions of 68—70
Esters, enolates of, alkylation of 28
Esters, enolates of, chelation of -alkoxy 69—70
Esters, enolates of, stereoselective formation 68 389—390
Esters, formate, formation of hydroxymethylene derivatives by 108—109
Esters, organozinc derivatives of 462
Esters, preparation, by acylation of alcohols 172
Esters, preparation, by alkylation of carboxylate ions 152—154
Esters, preparation, by Favorskii rearrangement 609—611
Esters, preparation, by Fischer esterification 172
Esters, preparation, by palladium-catalyzed carbonylation 521—525
Esters, preparation, from aldehydes by oxidation 795—796
Esters, preparation, from carboxylate salts by alkylation 153
Esters, preparation, from carboxylic acids by oxidative decarboxylation 792—793
Esters, preparation, from carboxylic acids using diazomethane 152—153
Esters, preparation, from ketones by Baeyer — Villiger oxidation 798—800
Esters, preparation, from organoboranes and -haloacetate esters 555—556
Esters, preparation, from ozonides 789
Esters, pyrolysis of 410—413
Esters, pyrolysis of, in synthesis of longifolene 868
Esters, reaction with organomagnesium compounds 446—447
Esters, reduction, by calcium borohydride 266
Esters, reduction, by lithium aluminum hydride 265
Esters, reduction, by lithium borohydride 266
Esters, thermal elimination 410—413
Esters, xanthate, pyrolysis of 413
Ethers, -hydroperoxy from ozonides 789
Ethers, alkenyl see “Enol ethers”
Ethers, allyl phenyl, Claisen rearrangement of 394
Ethers, allyl vinyl, Claisen rearrangement of 383—384
Ethers, cleavage of 159—161
Ethers, preparation by nucleophilic substitution 152
Favorskii rearrangement 609—611
Ferrocence 533
Fischer esterification 172
Fischer — Tropsch process 530
Fluoride ion, as catalyst for conjugate addition 41
Fluoride ion, in reactions of allylic silanes 573—574 576
Fluorination, aromatic 698
Fluorine, addition to alkenes 204—205
Formylation, aromatic 710—711
Fragmentation reactions 315 612—614 651 793—794
Fragmentation reactions, radical 674—679
Free radicals see “Radicals”
Friedel — Crafts acylation reactions 704—711
Friedel — Crafts acylation reactions, intramolecular 707
Friedel — Crafts acylation reactions, regioselectivity of 706
Friedel — Crafts alkylation reactions 699—704
Friedel — Crafts alkylation reactions, catalysts for 703
Friedel — Crafts alkylation reactions, chloromethylation 710
Friedel — Crafts alkylation reactions, intramolecular 704
Friedel — Crafts alkylation reactions, rearrangement during 702 704
Frontier orbitals of, 1,3-dipolarcycloadditions 360—362 366
Frontier orbitals of, Diels — Alder reactions 332—335
Frontier orbitals of, ene reactions 400
Frontier orbitals of, ketene cycloaddition reactions 368
Frontier orbitals of, radical reactions 657
Gif oxidation 809
Glycols see “1
Grignard reagents see “Magnesium organo-
Grob fragmentation 315 612—614
Halides, alkenyl, from alkenyl boranes 239—240
Halides, alkenyl, nickel-catalyzed coupling of 527
Halides, alkenyl, palladium-catalyzed coupling with alkenyl boranes 520—521
Halides, alkenyl, palladium-catalyzed reaction with alkenyl stannanes 511—515
Halides, alkenyl, palladium-catalyzed reaction with Grignard reagents 507—510
Halides, alkenyl, palladium-catalyzed reaction with organolithium compounds 507—510
Halides, alkenyl, palladium-catalyzed reaction with organozinc compounds 508
Halides, alkyl, by addition of hydrogen halides to alkenes 191—196
Halides, alkyl, enantioselective synthesis of 238
Halides, alkyl, preparation from alcohols 142—147
Halides, alkyl, reductive dehalogenation 288—290 296
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