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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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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
Aromatic substitution, by elimination-addition 724—728
Aromatic substitution, by metalation 711—714
Aromatic substitution, by the mechanism 734—736
Aromatic substitution, copper-catalyzed 728—730
Aromatic substitution, diazonium ions in 714—722
Aromatic substitution, electrophilic 693—714
Aromatic substitution, palladium-catalyzed 730—731
Azides, acyl, in Curtius rearrangement 646—648
Azides, alkyl, preparation by nucleophilic substitution 150—152
Azides, alkyl, reactions with ketones 650
Azides, alkyl, reactions with organoboranes 235
Azides, aryl, preparation from diazonium ions 721
Azides, aryl, reaction with organoboranes from 235
Azides, nitrenes from 642—644
Aziridines, equilibria with azomethine ylides 366
Aziridines, formation from nitrenoid additions 645
Azo compounds, thermal elimination of nitrogen from 405—408
Azomethine ylides, as dipolarophiles 366
Azomethines see “Imines”
Baeyer — Villiger oxidation 798—800
Baeyer — Villiger oxidation, in synthesis of Prelog — Djerassi lactone 870
Barbier reaction 458
Barton deoxygenation 290
Beckmann rearrangement 650—651
Benzene, chromium tricarbonyl complex of 534—535
Benzoxazolium salts, in preparation of alkyl halides 147
Benzo[c]furans, as dienes 347
Benzyne 724—728
Benzyne, as a dienophile 727
Benzyne, by diazotization of o-aminobenzoic acid 726—727
Benzyne, from benzothiadiazole-1,1-dioxide 727
Benzyne, from, 1-aminobenzotriazole 727
Betaine, as intermediate in Wittig reaction 111—112
Bicyclo[2.2.1]heptadien-7-ones, decarbonylation of 405 727
Biogenetic-type synthesis 98
Birch reduction 293—295
Birch reduction, in synthesis of juvabione 849
Birch reduction, in synthesis of longifolene 866
Borane see “Diborane”
Boranes, alkenyl, as dienophiles 344
Boranes, alkenyl, palladium-catalyzed coupling with alkenyl halides 520
Boranes, alkenyl, protonolysis 239
Boranes, alkyl, carbonylation of 549—555
Boranes, alkyl, conversion to amines 235
Boranes, alkyl, conversion to halides 235—236
Boranes, alkyl, fragmentation reaction of 613—614
Boranes, alkyl, hydroboration by 227 236—238 549—555
Boranes, alkyl, isomerization of 230—231
Boranes, alkyl, oxidation of 232—235
Boranes, alkyl, palladium-catalyzed coupling with halides 520
Boranes, alkyl, preparation of, by hydroboration 226—232
Boranes, alkyl, preparation of, from boron halides 548
Boranes, alkyl, preparation of, from cuprates 548
Boranes, alkyl, reactions of 232—236 549—563
Boranes, alkynyl, reactions with aldehydes and ketones 461
Boranes, allyl, preparation of 548
Boranes, allyl, reactions with aldehydes and ketones 559—563 872 880
Boranes, aryl, preparation of 548
Boranes, halo, as reducing agents 278—279
Boranes, halo, conversion to amines by azides 235
Boranes, halo, hydroboration by 228—229 233 235 553 555
Borinate esters 548
Boron enolates, aldol condensation reactions of 71—74
Boron enolates, from enones 72
Boron enolates, from ketones 71—72 86—87
Boron enolates, from silyl enol ethers 72
Boron tribromide, cleavage of ethers by 159
Boron trifluoride, cleavage of ethers by 163—164
Boron trifluoride, preparation of organoboranes from 548
Boronate esters 548
Boronate esters, alkenyl, as dienophiles 359
Boronate esters, aryl, preparation from aryllithium reagents and trialkyl borates 461—462
Boronate esters, B-allylic 548 559—563
Bromides see also “Halides”
Bromides, alkenyl, from alkynes by hydroboration 239
Bromides, alkyl, preparation, carboxylic acids 793
Bromides, alkyl, preparation, from alcohols 142—147
Bromides, alkyl, preparation, organoboranes 236
Bromides, aryl, preparation 697—698 717—721
Bromination, addition to alkenes 200—202
Bromination, aromatic 697
Bromine azide, as reagent 217
Bromohydrins, synthesis from alkenes 203—204
Bromonium ions 200—201
Cadmium, organo- compounds, preparation 463
Cadmium, organo- compounds, reaction with acid chlorides 464
Calcium borohydride 266
Carbanions see also “Enolates”
Carbanions, acylation of 101—110
Carbanions, conjugate addition reactions 39—45
Carbanions, formation by deprotonation 1—5
Carbanions, in aromatic substitution reactions 734—735
Carbanions, of phosphine oxides 117
Carbanions, phosphonate 116—117
Carbanions, resonance of 2
Carbanions, stabilization by substituents 3
Carbanions, trimethylsilyl, alkene forming reactions of 120—121
Carbenes and carbenoid intermediates 614—640
Carbenes and carbenoid intermediates, -acyl 621—622 633
Carbenes and carbenoid intermediates, addition reactions of 625—634
Carbenes and carbenoid intermediates, addition reactions of, enantioselective 637
Carbenes and carbenoid intermediates, generation of 620—625
Carbenes and carbenoid intermediates, insertion reactions 634—637 904
Carbenes and carbenoid intermediates, reactions with aromatic compounds 634
Carbenes and carbenoid intermediates, rearrangement reactions of 639—640
Carbenes and carbenoid intermediates, stereochemistry of addition reactions 618 625—626
Carbenes and carbenoid intermediates, structures of 614—619
Carbenes and carbenoid intermediates, substituent effects on reactivity and structure 618—619
Carbenes and carbenoid intermediates, ylides from 637—639
Carbobenzyloxy groups, as protecting groups for amines 260 831
Carbocations, as intermediates in 595—602
Carbocations, as intermediates in, addition of hydrogen halides to alkenes 191—195
Carbocations, as intermediates in, chlorination of alkenes 202
Carbocations, as intermediates in, Friedel — Crafts alkylation 699—704
Carbocations, as intermediates in, polyene cyclization 598—601
Carbocations, fragmentation reactions of 612—614
Carbocations, reactions with, alkenes 595—596
Carbocations, reactions with, silyl enol ethers 596—597
Carbocations, reactions with, unsaturated silanes 567—573
Carbocations, reactions with, unsaturated stannanes 579—585
Carbocations, rearrangements of 193—202 602—609
Carbocations, rearrangements of, in synthesis of longifolene 838
Carbon acids, pK of 3—4
Carbonate esters, as protecting groups for diols 831
Carbonylation, of organoboranes 549—555
Carbonylation, palladium-catalyzed 521—525
Carbonylation, rhodium-catalyzed 529—530
Carboxylation. of ketones 166—171
Carboxylic acids, -diazo. reaction with ketones 609
Carboxylic acids, -halogenation 220
Carboxylic acids, -hydroxy, oxidative decarboxylation to ketones 794
Carboxylic acids, -keto, oxidation to enones 794
Carboxylic acids, -keto, synthesis of 108—109
Carboxylic acids, acylation reagents from 166—171
Carboxylic acids, amides from 172—179
Carboxylic acids, cesium salts, alkylation of 153
Carboxylic acids, dianions of, alkylation of 28
Carboxylic acids, enantioselective synthesis of 30—31 36—39
Carboxylic acids, esterification, by diazomethane 152
Carboxylic acids, esterification, Fischer 172
Carboxylic acids, homologation 642
Carboxylic acids, Hunsdiecker reaction 793
Carboxylic acids, oxidative decarboxylation of 792—794
Carboxylic acids, preparation from, aldehydes by oxidation 788 795
Carboxylic acids, preparation from, Grignard reagents and carbon dioxide 451
Carboxylic acids, preparation from, methyl ketones by hypohalite oxidation 803
Carboxylic acids, protecting groups for 837—838
Carboxylic acids, pyridine-2-thiol esters as acylating agents 170
Carboxylic acids, reduction by diborane 270
Carboxylic acids, unsaturated, ,-synthesis 101
Carboxylic acids, unsaturated, enantioselective hydrogenation 256—259
Carboxylic acids, unsaturated, iodolactonization of 205—206
Catechol borane, hydroboration by 229—230 239
Catechol borane, in enantioselective reduction 279
Cerium, organo- compounds reactions with, carboxylate salts 468
Cerium, organo- compounds reactions with, hydrazones 468
Cerium, organo- compounds reactions with, ketones 467
Chelation in, addition of allylic stannanes to aldehydes 582—583
Chelation in, aromatic thallation 714
Chelation in, Claisen rearrangement of -amino esters 392
Chelation in, enolate of -alkoxy esters 391
Chelation in, Grignard addition reactions of -alkoxyketones 458
Chelation in, reactions of N-methyl-N-methoxyamides 457
Cheletropic elimination 403—405
Chiral auxiliary in, aldol addition reactions 84—86
Chiral auxiliary in, Diels — Alder reactions 349—352
Chiral auxiliary in, iodocyclization 207
Chiral auxiliary in, multi-step synthesis 848
Chiral auxiliary in, sigmatropic rearrangements 393
Chlorides see also “Halides”
Chlorides, alkyl, preparation from, alcohols 142—147
Chlorides, alkyl, preparation from, alkenes 191—195
Chlorination, aromatic 695—697
Chlorination, of alkenes 201—202
Chlorination, of alkynes 225—226
Chromium(VI) oxidants, allylic oxidation of alkenes 804
Chromium(VI) oxidants, of alcohols 747—752
Chromium(VI) oxidants, oxidation of saturated hydrocarbons 807—808
Chromium, -complexes with aromatics 534—535
Claisen condensation 57 101—107
Claisen rearrangement 383—394
Claisen rearrangement, of allyl vinyl ethers 383—384
Claisen rearrangement, of ester silyl enol ethers 389—392
Claisen rearrangement, of ester silyl enol ethers, steric effects on rate 390
Claisen rearrangement, of O-allyl orthoesters 384—388
Claisen rearrangement, stereoselectivity of 388
Claisen — Schmidt condensation 60—62
Clark — Eschweiler reductive alkylation 288
Clemmensen reduction 307
Cobalt salts, as catalysts for organometallic coupling 531
Collin's reagent 750
Combinatorial synthesis 903—908
Concerted reactions 331
Conjugate addition reactions 39—47
Conjugate addition reactions, in Robinson annulation reaction 89—95
Conjugate addition reactions, kinetic conditions for 44—45
Conjugate addition reactions, of organocopper reagents 480 487—494
Conjugate addition reactions, stereoselectivity of 42—45
Conjugate addition reactions, tandem alkylation and 44—45
Convergent synthesis 846
Cope rearrangement 376—383
Cope rearrangement, aza-Cope rearrangement 574
Cope rearrangement, catalysis by Pd(II) salts 380—382
Cope rearrangement, enantioselectivity of 379—380
Cope rearrangement, of divinylcyclopropanes 380
Cope rearrangement, oxy- see “Oxy-Cope rerrangement”
Cope rearrangement, stereoselectivity of 376—380
Copper oxazoline complexes, as catalysts 353 401 630—631
Copper salts, as catalysts for, aziridination of alkenes 645
Copper salts, as catalysts for, carbenoid additions 630
Copper salts, as catalysts for, nucleophilic aromatic substitution 728—730
Copper(I) bromide, in preparation of organocopper reagents 481
Copper(I) bromide, in Sandmeyer reaction 717
Copper(I) trifluoromethanesulfonate, as catalyst for, alkene photocycloaddition 371—372
Copper(I) trifluoromethanesulfonate, as catalyst for, carbenoid additions 630
Copper(I) trifluoromethanesulfonate, as catalyst for, coupling of aryl halides 495
Copper(I) trifluoromethanesulfonate, as catalyst for, nucleophilic aromatic substitution 730
Copper(II) bromide, bromination of ketones by 218
Copper, organo- compounds 477—498
Copper, organo- compounds, addition to, acetylenic esters 493
Copper, organo- compounds, addition to, alkynes 495
Copper, organo- compounds, addition to, unsaturated carbonyl compounds 488—493
Copper, organo- compounds, alkenyl, preparation, from alkenyl stannanes 480
Copper, organo- compounds, alkenyl, preparation, from alkynes 480
Copper, organo- compounds, as intermediates in, conjugate addition of Grignard reagents to enones 478
Copper, organo- compounds, cuprates, 2-thienyl 479—481
Copper, organo- compounds, cuprates, cyano 479—481
Copper, organo- compounds, cuprates, mixed 479—481
Copper, organo- compounds, cuprates, zinc reagents 489—491 495
Copper, organo- compounds, organoboranes from 584
Copper, organo- compounds, preparation of 477—481
Copper, organo- compounds, reactions of with, allylic esters 485—486
Copper, organo- compounds, reactions of with, epoxides 487
Copper, organo- compounds, reactions of with, Grignard reagents 486—487
Copper, organo- compounds, reactions of with, halides 481—485
Copper, organo- compounds, reactions of with, propargylic systems 486
Copper, organo- compounds, reactions of with, unsaturated carbonyl compounds 488—493
Copper, organo- compounds, structure of 478
Crown ethers, catalysis by 149 623
Crown ethers, solvation by 23 25
Cuprates see “Copper organo-”
Curtius rearrangement 646
Cyanide, conjugate addition of 46
Cyanoethyl, as protecting group 901
Cyanohydrins, as intermediates in oxidation of aldehydes 786
Cyanohydrins, ethers of, as acyl anion equivalents 839 853
Cycloaddition reactions 331—376
Cycloaddition reactions, 1,3-dipolar 359—367
Cycloaddition reactions, Diels — Alder 332—359
Cycloaddition reactions, of ketenes 367—370
Cycloaddition reactions, photochemical 370—376
Cycloaddition reactions, photochemical, in synthesis of longifolene 866
Cyclobutadiene, iron tricarbonyl complex of 532—533
Cyclobutanes, preparation of, by photochemical cycloaddition 370—374
Cyclobutanes, preparation of, by [2+2] cycloadditions 367—374
Cyclobutanes, preparation of, from azo compounds 406
Cyclobutanones, by ketene cycloaddition 368—370
Cycloheptatrienes, from aromatics by carbene addition 634
Cycloheptatrienylidene, structure 619
Cyclohexanones, enamines of 32
Cyclohexanones, enolates of, intramolecular alkylation 19—20
Cyclohexanones, enolates of, stereoselective alkylation 17—18
Cyclohexanones, N,N-dimethylhydrazone, alkylation of 38
Cyclopentadienones, Diels — Alder addition reactions of 405
Cyclopropanes, divinyl, Cope rearrangement of 380
Cyclopropanes, preparation from, alkenes by carbene addition 623 625—634
Cyclopropanes, preparation from, enones and sulfur ylides 125
Cyclopropanes, preparation from, pyrazolines 362 404
Cyclopropanones, as intermediates in Favorskii rearrangement 611
Cyclopropanones, conversion to oxyallyl ions 366—367
Cyclopropenes, from alkenyl carbenes 640
Cyclopropenylidene, structure 619
Cyclopropylcarbinyl radicals, fragmentation of 676—677
Cyclopropylidenes, ring-opening to allenes 640
Danishefsky's diene 345
Darzens reaction 127
DDQ see “Dichlorodicyanoquinone”
Decalone, alkylation of enolates of 18—19
Decarbonylation, of acid chlorides 431
Decarbonylation, of aldehydes 431
Decarbonylation, of bicyclo[2.2.1]heptadien-7-ones 404—405 727
Decarboxylation, during amine-catalyzed condensations 101
Decarboxylation, of -keto acids 15 883
Decarboxylation, of malonic acid derivatives 15
Decarboxylation, of N-hydroxy-2-thiopyridone esters 653 675—676
Decarboxylation, of trichoroacetic acid, dichlorocarbene from 624
Decarboxylation, oxidative 792—794
Decarboxylation, via radical intermediates 676
Dess — Martin reagent 755
Dianions, generation and alkylation 20
Diazaboridines, as chiral auxiliaries 563
Diazaboridines, as enantioselective catalysts 88 352 391
Diazenes, elimination of nitrogen from 403—404
Diazirines, carbenes from 623
Diazirines, preparation of 623
Diazo compounds, carbenes from 620—622 630—634
Diazo compounds, cycloaddition reactions 359 362 866
Diazo compounds, from N-aziridinoimines 866
Diazo compounds, metal ion-catalyzed reactions of 630—633 635—637 639
Diazo compounds, preparation of 620—623
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