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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
Halides, aryl, copper-catalyzed coupling      495—498
Halides, aryl, nickel-catalyzed coupling of      527
Halides, aryl, nickel-catalyzed coupling with Grignard reagents      528
Halides, aryl, palladium-catalyzed alkenylation of      503—507
Halides, aryl, palladium-catalyzed coupling with alkenyl stannanes      511—514
Halides, aryl, palladium-catalyzed coupling with alkyl boranes      515—519
Halides, aryl, palladium-catalyzed coupling with arylboronic acids      515—519
Halides, aryl, palladium-catalyzed reactions with organozinc compounds      509
Halides, aryl, preparation from diazonium intermediates      717—721
Halides, reductive dehalogenation of      280 283—284 288—290 296
Halogenation, aromatic      695—699
Halogenation, of acid halides      220
Halogenation, of alkenes      202—205
Halogenation, of alkynes      225—226
Halogenation, of ketones      216—220
Halogenation, reagents for      209—210
Halogenation, stereoselectivity of      201—202
Hard-soft-acid-base theory, application to enolate alkylation      25
Heck reaction      503—507
Heck reaction, intramolecular in Taxol synthesis      885
Hexamethylphosphoric triamide (HMPA), solvation by      21—25 149 280 389 438
HMPA      see “Hexamethylphosphoric triamide”
Hofmann — Loeffler reaction      655
Hofrnann rearrangement      646—648
Homoenolate anion, synthetic equivalents for      841
Horner — Wittig reaction      117
Hunsdiecker reaction      793
Hydrazones, chiral, enantioselective alkylation of      38
Hydrazones, diazo compounds from      621
Hydrazones, hydrolysis to ketones      38
Hydrazones, N,N-dimethyl, alkylation of anions of      38
Hydrazones, radical addition to      666
Hydrazones, sulfonyl, diazo compounds from      623
Hydrazones, sulfonyl, Shapiro reaction of      309—310
Hydrazones, Wolff — Kishner reduction of      307—308
Hydroboration      226—232
Hydroboration, catalysis of      229—230
Hydroboration, enantioselective      230 236—238
Hydroboration, of 1,5-dienes      871
Hydroboration, of alkynes      239—240
Hydroboration, regioselectivity of      226—227
Hydroboration, stereoselectivity of      227—228
Hydroboration, thermal reversibility of      230—232
Hydroformylation      529—530
Hydrogen atom donors      208—209 290 314 658 664 716
Hydrogen peroxide, in epoxidation      770
Hydrogenation      249—261
Hydrogenation, by dimide      262
Hydrogenation, catalysts for homogeneous      253—259
Hydrogenation, enantioselective      253—259
Hydrogenation, isomerization during      250
Hydrogenation, mechanism of      250
Hydrogenation, stereoselectivity of      252
Hydrogenolysis      260
Hydrosilation      563 567
Hydroxymethylene derivatives, synthesis of      109
Hypohalites, acyl, as halogenating agents      698—699
Hypohalites, ions, in oxidation of methyl ketones      803
Imidazolides      see “Acyl imidazolides”
Imides, reduction of      99
Imines, addition reactions of      96—100
Imines, anions, alkylation of      31—37
Imines, anions, alkylation of, enantioselective      37—38
Imines, anions, alkylation of, regioselectivity of      37—38
Imines, formation by rearrangement of alkyl nitrenes      644
Imines, reactions with unsaturated silanes      574—575
Imines, reduction by sodium cyanoborohydride      269
Iminium ions, reactions with unsaturated silanes      574
Imino ethers, synthesis of      156
Iodides      see “Halides”
Iodides, alkenyl, from alkynes via hydroboration      239—240
Iodides, alkyl, preparation from alcohols      146
Iodides, alkyl, reduction by hydride donors      283—284
Iodides, aryl, preparation, by halogenation      688—689
Iodides, aryl, preparation, from diazonium ions      719 721
Iodination, aromatic      688—689
Iodine azide, as reagent      217
Iodine isocyanate, as reagent      217
Iodine nitrate, as reagent      217
Iodine thiocyanate, as reagent      217
Iodolactonization      205—207
Iridium catalysts for homogeneous hydrogenation      253
Isobenzofurans, as Diels — Alder dienes      347
Isoxazoles, from alkenes and nitrile oxides by cycloaddition      365
Isoxazolines, from alkenes and nitrones by cycloaddition      364—365
Jones reagent      748
Julia — Lythgoe alkene synthesis      314
Juvabione, synthesis of      848—859
Ketals, alkenyl, as dienophiles      343—344
Ketals, as protective groups      822—824 829 835—836
Ketenes, as intermediates in diazoketone rearrangements      641—642
Ketenes, dienophilic synthetic equivalent for      341—342
Ketenes, [2 + 2]cycloaddition reactions of      367—369
Ketones, $\alpha$-acetoxy, by oxidation with lead tetraacetate      796
Ketones, $\alpha$-acetoxy, from enol acetates by epoxidation      779
Ketones, $\alpha$-acetoxy, reduction of      298
Ketones, $\alpha$-alkoxy, reaction with Grignard reagents      458
Ketones, $\alpha$-alkoxy, stereoselective reduction      276
Ketones, $\alpha$-allyloxy, Claisen rearrangement of enolate      391
Ketones, $\alpha$-bromo, enolates from      462
Ketones, $\alpha$-bromo, formation of      216—218
Ketones, $\alpha$-chloro      219
Ketones, $\alpha$-diazo, preparation of      621—622
Ketones, $\alpha$-diazo, reaction with organoboranes      556
Ketones, $\alpha$-diazo, rhodium-catalyzed carbenoid reactions of      632—633 636—637
Ketones, $\alpha$-diazo, Wolff rearrangement      641—642
Ketones, $\alpha$-fluoro      219—220
Ketones, $\alpha$-halo, Favorskii rearrangement of      609—611
Ketones, $\alpha$-halo, formation from alkenyl halides by epoxidation      779
Ketones, $\alpha$-halo, reaction with organoboranes      555—556
Ketones, $\alpha$-halo, zinc enolates from      462
Ketones, $\alpha$-hydroxy, preparation of      305—306 779 796—798 800
Ketones, $\alpha$-hydroxy, stereoselective reduction      276—277
Ketones, $\alpha,\beta$-unsaturated, addition of organocopper reagents to      487—493
Ketones, $\alpha,\beta$-unsaturated, alkenyl stannanes and alkenyl trifluorome-thanesulfonates by carbonylation      521—523
Ketones, $\alpha,\beta$-unsaturated, conjugate addition reactions of      39—45 89—95
Ketones, $\alpha,\beta$-unsaturated, deprotonation of      5—10
Ketones, $\alpha,\beta$-unsaturated, enolates of      9—10 26
Ketones, $\alpha,\beta$-unsaturated, epoxidation by peroxides      767
Ketones, $\alpha,\beta$-unsaturated, from aldol condensation reactions      58—60
Ketones, $\alpha,\beta$-unsaturated, from alkenyl mercury compounds and acid chlorides      465
Ketones, $\alpha,\beta$-unsaturated, photocycloaddition reactions of      372—374
Ketones, $\alpha,\beta$-unsaturated, reactions with allylic silanes      580 584
Ketones, $\alpha,\beta$-unsaturated, reactions with organolithium compounds      453
Ketones, $\alpha,\beta$-unsaturated, reactions with sulfur ylides      122—126
Ketones, $\alpha,\beta$-unsaturated, reduction of      11 272—273 292—293
Ketones, $\alpha,\beta$-unsaturated, tandem conjugate addition-alkylation of      489—490
Ketones, $\alpha,\beta$-unsaturated, trimethylsilyl enol ethers from      11
Ketones, $\beta,\gamma$-unsaturated by alkene arylation      598
Ketones, acylation      108—109
Ketones, Baeyer — Villiger oxidation of      798—800
Ketones, conversion to carboxylic acids by haloform reaction      803
Ketones, enantioselective reduction      278—280
Ketones, enantioselective synthesis of      36—38 493—494 553—554
Ketones, enolates, stereoselective formation      5—10
Ketones, halogenation of      216—219
Ketones, hindered, reaction with organocerium reagents      467
Ketones, hindered, reduction by Grignard reagents      447
Ketones, hindered, Wittig reaction of      112
Ketones, oxidation of      794—803
Ketones, oxidation of, $MoO_5$ pyridine HMPA      798
Ketones, oxidation of, Cr(VI) reagents      794—795
Ketones, oxidation of, lead tetraacetate      796
Ketones, oxidation of, N-sulfonyloxaziridines      797—798
Ketones, oxidation of, peroxy acids      798—800
Ketones, oxidation of, selenium dioxide      802
Ketones, photocycloaddition reactions of      372 374—376
Ketones, preparation from, $\alpha$-hydroxy carboxylic acids by oxidative decarboxylation      794
Ketones, preparation from, acid chlorides and Grignard reagents      451
Ketones, preparation from, acid chlorides and organocadmium reagents      464
Ketones, preparation from, acid chlorides and organocopper reagents      485
Ketones, preparation from, acid chlorides and stannanes      525
Ketones, preparation from, alcohols by oxidation      747—757
Ketones, preparation from, alkenes by hydroboration-oxidation      232—235 237—238
Ketones, preparation from, alkenes by palladium-catalyzed oxidation      501
Ketones, preparation from, alkenyl silanes and acid chlorides      568
Ketones, preparation from, alkenyl silanes by epoxidation      780
Ketones, preparation from, alkyl halides by carbonylation      522
Ketones, preparation from, alkynes by hydration      224—225
Ketones, preparation from, aminomethyl carbinols by rearrangement      608
Ketones, preparation from, aromatics by Friedel — Crafts acylation      704—710
Ketones, preparation from, carboxylic acids and organolithium reagents      453—456
Ketones, preparation from, epoxides by Lewis acid-catalyzed rearrangement      778
Ketones, preparation from, nitrites and Grignard reagents      449—450
Ketones, preparation from, organoboranes by carbonylation      550—555
Ketones, protecting groups for      835—837
Ketones, reactions of, with, allylic silanes      568—571 574
Ketones, reactions of, with, azides      650
Ketones, reactions of, with, diazoalkanes      608—609
Ketones, reactions of, with, hydrazoic acid      649
Ketones, reactions of, with, organolithium compounds      453—456
Ketones, reactions of, with, organomagnesium compounds      446—450 457—458
Ketones, reactions of, with, sulfur ylides      122—126
Ketones, reduction by, dissolving metals      292—293 299—305
Ketones, reduction by, Grignard reagents      447
Ketones, reduction by, hydride exchange      287—288
Ketones, reduction by, hydride-donor reagents      262—267 273—280
Ketones, reduction by, silanes      286—287
Ketones, reductive coupling of      299—305
Ketones, reductive deoxygenation of      307—310
Ketones, ring expansion of cyclic      608—609
Ketones, stereoselective reduction of      273—280
Knoevenagel condensation      100—101
Lactams, by iodocyclization of O,N-trimethylsilyl imidates      207
Lactones, $\alpha$-methylene, sythesis      98
Lactones, formation of      170—171 522 636 655 659 801
Lactones, macrocyclic      171—172
Lactones, protection as dithioketals      838
Lactones, reduction of      266
Lanthanide salts, as catalysts, 1,3-dipolar cycloaddition      365
Lanthanide salts, as catalysts, addition reactions of allylic silanes      570
Lanthanide salts, as catalysts, alcohol acylation      167
Lanthanide salts, as catalysts, aromatic nitration      697
Lanthanide salts, as catalysts, Baeyer — Villager reaction      799
Lanthanide salts, as catalysts, conjugate addition      45
Lanthanide salts, as catalysts, Diels — Alder reaction      339 350
Lanthanide salts, as catalysts, ene reactions of aldehydes      401
Lanthanide salts, as catalysts, epoxide ring opening      775
Lanthanide salts, as catalysts, Friedel — Crafts reactions      704
Lanthanide salts, as catalysts, Fries rearrangement      710
Lanthanide salts, as catalysts, hydride transfer      287—288
Lanthanide salts, as catalysts, Mukaiyama reaction      79
Lanthanides, organo- compounds      467—468
Lead tetraacetate, amides, oxidation of      649
Lead tetraacetate, diols, cleavage of      791
Lead tetraacetate, oxidative cyclization of alcohols by      655—656
Lead tetraacetate, oxidative decarboxylation of carboxylic acids      792—794
Lewis acid catalysis for, addition of diazo compounds to ketones      609
Lewis acid catalysis for, addition of silanes to aldehydes      568—573
Lewis acid catalysis for, addition of stannanes to aldehydes      580—585
Lewis acid catalysis for, aromatic halogenation      697
Lewis acid catalysis for, Diels — Alder reactions      336—338 349—350 355
Lewis acid catalysis for, dioxolane formation      835
Lewis acid catalysis for, ene reactions      401—403
Lewis acid catalysis for, Friedel — Crafts reactions      697—711
Lewis acid catalysis for, Mukaiyama reaction      79 82
Lindlar's catalyst      260
Lithium tri-t-butoxyaluminum hydride      267
Lithium trialkylborohydrides, as reducing agents      267 276 278
Lithium triethylborohydride      284 776
Lithium, organo- compounds, alkenyl, alkylation of      445
Lithium, organo- compounds, alkenyl, preparation by Shapiro reaction      444 885
Lithium, organo- compounds, alkylation of      445—446
Lithium, organo- compounds, alkynyl      438
Lithium, organo- compounds, allylic, alkylation of      445
Lithium, organo- compounds, benzylic, alkylation of      445
Lithium, organo- compounds, configurational stability of      442
Lithium, organo- compounds, cyclization of      452
Lithium, organo- compounds, organoboranes from      548
Lithium, organo- compounds, preparation of      436—437
Lithium, organo- compounds, preparation of, by lithiation      438—441
Lithium, organo- compounds, preparation of, from halides by halogen-metal exchange      442—443
Lithium, organo- compounds, preparation of, from hydrazones by Shapiro reaction      444 885
Lithium, organo- compounds, preparation of, from stannanes by metal-metal exchange      443—444
Lithium, organo- compounds, preparation of, from sulfides by reduction      437
Lithium, organo- compounds, reaction with, carbonyl compounds      447—449 457—458
Lithium, organo- compounds, reaction with, carboxylic acids      453
Lithium, organo- compounds, reaction with, halostannanes      579
Lithium, organo- compounds, reaction with, N-methoxy-N-methylamides      456—457
Lithium, organo- compounds, reaction with, trimethylsilyl chloride      563—566
Lithium, organo- compounds, structure of      438—439
Lombardo's reagent      462
Longifolene, synthesis of      859—869
Magnesium, organo- compounds, alkylation of      446 486—487
Magnesium, organo- compounds, alkynyl      438
Magnesium, organo- compounds, copper-catalyzed conjugate addition of      494—497
Magnesium, organo- compounds, cyclopropylmethyl, ring-opening of      452
Magnesium, organo- compounds, mixed copper reagents      495
Magnesium, organo- compounds, nickel-catalyzed coupling      528
Magnesium, organo- compounds, organoboranes from      548
Magnesium, organo- compounds, preparation of      434—435 438
Magnesium, organo- compounds, reactions with, acid chlorides      451
Magnesium, organo- compounds, reactions with, aldehydes      446—450
Magnesium, organo- compounds, reactions with, amides      451
Magnesium, organo- compounds, reactions with, carbon dioxide      451
Magnesium, organo- compounds, reactions with, esters      447—448
Magnesium, organo- compounds, reactions with, halostannanes      579
Magnesium, organo- compounds, reactions with, ketones      446—450 457—458
Magnesium, organo- compounds, reactions with, nitrites      450
Magnesium, organo- compounds, reactions with, triethyl orthoformate      451
Magnesium, organo- compounds, reactions with, trimethylsilyl chloride      563 566
Magnesium, organo- compounds, stereochemistry of      435—436
Magnesium, organo- compounds, structure of      434 436 452
Magnesium, organo- compounds, unsaturated, isomerization of      451—452
Malonate ester anions acylation of      105 108
Malonate ester anions acylation of, alkylation of      11—13
Malonate ester anions acylation of, as enolate synthetic equivalents      13
Malonate ester anions acylation of, cyclization of $\omega$-haloalkyl      13
Malonate ester anions acylation of, reaction with $\pi$-allylpalladium compounds      510
Malonic acids, decarboxylation of      13
Malonic acids, in Knoevenagel condensation      101
Mannich reaction      96—99
Markownikoff's rule      191—192
Meerwein arylation reaction      722
Meerwein — Pondorff — Verley reduction      287
Mercurinium ion intermediate      196
Mercury compounds, organo-      464—465
Mercury compounds, organo-, $\alpha$-acetoxy      659
Mercury compounds, organo-, aromatic      711—713
Mercury compounds, organo-, carbenes from      625 633
Mercury compounds, organo-, preparation of      196—200 464—465 659
Mercury compounds, organo-, reactions of      465
Mercury compounds, organo-, reduction by sodium borohydride      196—198 659
Mercury salts in, aromatic halogenation      698
Mercury salts in, aromatic mercuration      711—713
Mercury salts in, initiation of polyene cyclization by      600
Mercury salts in, oxymercuration reactions      196—200
Mercury salts in, ring-opening of cyclopropanes by      856
Michael reaction      see “Conjugate addition”
Michaelis — Arbuzov reaction      158
Mitsunobu reaction, in nitrogen alkylation      157
Mitsunobu reaction, in preparation of alkyl azides      151
Mitsunobu reaction, in preparation of alkyl iodides      146
Mitsunobu reaction, inversion of alcohol configuration by      153—154
Mukaiyama reaction      78—82
Mukaiyama reaction, in synthesis of Taxol      887
Mukaiyama reaction, intramolecular in synthesis of longifolene      868
N-bromosuccinimide, aromatic bromination      697
N-bromosuccinimide, bromination of ketones by      216—219
N-bromosuccinimide, bromohydrins from alkenes by      203
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