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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
Aromatic substitution, by elimination-addition      724—728
Aromatic substitution, by metalation      711—714
Aromatic substitution, by the $S_{RN}1$ 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 $S_{RN}1$ 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, $\alpha$-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, $\alpha$-diazo. reaction with ketones      609
Carboxylic acids, $\alpha$-halogenation      220
Carboxylic acids, $\alpha$-hydroxy, oxidative decarboxylation to ketones      794
Carboxylic acids, $\beta$-keto, oxidation to enones      794
Carboxylic acids, $\beta$-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, $\alpha,\beta$,-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 $\alpha$-amino esters      392
Chelation in, enolate of $\alpha$-alkoxy esters      391
Chelation in, Grignard addition reactions of $\alpha$-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, $\pi$-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 $\beta$-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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