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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
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, -acetoxy, by oxidation with lead tetraacetate 796
Ketones, -acetoxy, from enol acetates by epoxidation 779
Ketones, -acetoxy, reduction of 298
Ketones, -alkoxy, reaction with Grignard reagents 458
Ketones, -alkoxy, stereoselective reduction 276
Ketones, -allyloxy, Claisen rearrangement of enolate 391
Ketones, -bromo, enolates from 462
Ketones, -bromo, formation of 216—218
Ketones, -chloro 219
Ketones, -diazo, preparation of 621—622
Ketones, -diazo, reaction with organoboranes 556
Ketones, -diazo, rhodium-catalyzed carbenoid reactions of 632—633 636—637
Ketones, -diazo, Wolff rearrangement 641—642
Ketones, -fluoro 219—220
Ketones, -halo, Favorskii rearrangement of 609—611
Ketones, -halo, formation from alkenyl halides by epoxidation 779
Ketones, -halo, reaction with organoboranes 555—556
Ketones, -halo, zinc enolates from 462
Ketones, -hydroxy, preparation of 305—306 779 796—798 800
Ketones, -hydroxy, stereoselective reduction 276—277
Ketones, -unsaturated, addition of organocopper reagents to 487—493
Ketones, -unsaturated, alkenyl stannanes and alkenyl trifluorome-thanesulfonates by carbonylation 521—523
Ketones, -unsaturated, conjugate addition reactions of 39—45 89—95
Ketones, -unsaturated, deprotonation of 5—10
Ketones, -unsaturated, enolates of 9—10 26
Ketones, -unsaturated, epoxidation by peroxides 767
Ketones, -unsaturated, from aldol condensation reactions 58—60
Ketones, -unsaturated, from alkenyl mercury compounds and acid chlorides 465
Ketones, -unsaturated, photocycloaddition reactions of 372—374
Ketones, -unsaturated, reactions with allylic silanes 580 584
Ketones, -unsaturated, reactions with organolithium compounds 453
Ketones, -unsaturated, reactions with sulfur ylides 122—126
Ketones, -unsaturated, reduction of 11 272—273 292—293
Ketones, -unsaturated, tandem conjugate addition-alkylation of 489—490
Ketones, -unsaturated, trimethylsilyl enol ethers from 11
Ketones, -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, 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, -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, -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 -haloalkyl 13
Malonate ester anions acylation of, reaction with -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-, -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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