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Carey F.A., Sundberg R.J. — Advanced organic chemistry (Part B)
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.


ßçûê: en

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
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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 $\alpha$-      623—625
Elimination reactions, cheletropic      403—404
Elimination reactions, of $\beta$-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 $\beta$-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 $\alpha,\beta$-enones      11 292—293
Enolates, formation of, enantioselective      8—9
Enolates, formation of, from $\alpha,\beta$-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 $S_{RN}1$ substitution reactions      734—735
Enolates, in Robinson annulation reaction      89—95
Enolates, magnesium, acylation of      105—108
Enolates, of $\alpha,\beta$-unsaturated ketones, alkylation      27
Enolates, of $\alpha,\beta$-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, $\mathrm{MoO}_5$-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, $\alpha$-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, $\alpha$-alkoxy, aldol addition of enolates      68—70
Esters, $\alpha$-alkoxy, Claisen rearrangement of silyl enol ethers      389—391
Esters, $\alpha$-alkoxy, enolates of      391
Esters, $\alpha$-diazo, reaction with organoboranes      556
Esters, $\alpha$-diazo, rhodium-catalyzed carbenoid reactions of      636—637
Esters, $\alpha,\beta$-unsaturated, addition of organocopper reagents to      489
Esters, $\alpha,\beta$-unsaturated, copper-catalyzed addition of Grignard reagents      494—495
Esters, $\alpha,\beta$-unsaturated, preparation by palladium-catalyzed carbonylation      521
Esters, $\alpha,\beta$-unsaturated, reaction with allylic silanes      576
Esters, $\alpha,\beta$-unsaturated, reduction of      272
Esters, $\beta$-keto, alkylation of      11—14 23—25 41
Esters, $\beta$-keto, reaction with $\pi$-allylpalladium compounds      501
Esters, $\beta$-keto, synthesis by enolate acylation      101—109
Esters, $\beta$-sulfonyl, reaction with $\pi$-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 $\alpha$-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 $\alpha$-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, $\alpha$-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
1 2 3 4 5 6
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