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

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Ќазвание: Advanced organic chemistry (Part B)

јвторы: Carey F.A., Sundberg R.J.

јннотаци€:

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.


язык: en

–убрика: ’ими€/

—татус предметного указател€: √отов указатель с номерами страниц

ed2k: ed2k stats

»здание: 4th edition

√од издани€: 1938

 оличество страниц: 965

ƒобавлена в каталог: 16.04.2006

ќперации: ѕоложить на полку | —копировать ссылку дл€ форума | —копировать ID
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ѕредметный указатель
$\alpha$-diones, cleavage by periodate      791
$\alpha$-diones, preparation by, oxidation of alkynes      758
$\alpha$-diones, preparation by, oxidation of enamino ketones      785
$\alpha$-diones, preparation by, oxidation of ketones by selenium dioxide      802
$\beta$-diketones, alkylation of      13Ч14
$\beta$-ketoacids, decarboxylation of      14
$\pi$-allyl complexes, of nickel      532
$\pi$-allyl complexes, of palladium      499Ч500 532
1,2-diols, cleavage by, lead tetraacetate      791
1,2-diols, cleavage by, periodate      757 790Ч791
1,2-diols, monotosylates, rearrangement of      604Ч607
1,2-diols, preparation by, epoxide ring-opening      772Ч774
1,2-diols, preparation by, hydroxylation of alkenes      757Ч760
1,2-diols, preparation by, oxymercuration of allylic alcohols      200
1,2-diols, preparation by, reductive coupling of carbonyl compounds      299 304
1,2-diols, protecting groups for      829
1,2-diols, rearrangements of      602Ч607
1,2-diols, reductive deoxygention      312Ч314
1,3-diols, fragmentation of      613Ч614
1,3-dipoles      359
1,5-dienes, hydroboration of      871
1,5-dienes, [3,3]-sigmatropic rearrangements of      376Ч382
1-hydroxybenzotriazole, in activation of carboxylic acids      176
1-hydroxybenzotriazole, in peptide coupling      899
2,5-dihydrothiophene-1,1-dioxides, dienes from      404
2,5-dihydrothiophene-1,1-dioxides, quinodimethanes from      404
2-chloro-3-ethylbenzoxazolium ion, conversion of alcohols to chlorides by      147
2-chloro-l-methylpyridinium ion, activation of carboxylic acids by      169Ч170
2-chloroisoxazolium ion, activation of carboxylic acids by      169
2-fluoro-l-methylpyridinium ion, in preparation of azides from alcohols      151
4-dimethylaminopyridine, as acylation catalyst      167 169 171 829
4-methoxyphenyl, as hydroxyl protecting group      827
4-pentenoyl, as amine protecting group      834
Acetals, as carbonyl-protecting groups      835
Acetals, as diol-protecting groups      829
Acetals, reactions with, allylic silanes      572Ч573
Acetals, reactions with, allylic stannaries      583
Acetals, reactions with, silyl enol ethers      82
Acetoacetate carbanions, acylation of      108
Acetoacetate carbanions, as enolate synthetic equivalents      13
Acetoacetate carbanions, O- versus C- alkylation of      23Ч25
Acetonides, as diol-protecting groups      829
Acid chlorides, acylation of alcohols by      166
Acid chlorides, acylation of enolates by      108
Acid chlorides, decarbonylation of      431
Acid chlorides, halogenation of      220
Acid chlorides, preparation of      166
Acid chlorides, reaction with, alkenyl silanes      568
Acid chlorides, reaction with, allylic silanes      568
Acid chlorides, reaction with, organocadmium compounds      463
Acyl anions, synthetic equivalents for      839Ч841
Acyl imidazolides, acylation of carbanion by      107
Acyl imidazolides, ester formation by      168Ч169 829Ч830
Acyl iminium ions, addition reactions of      99Ч100
Acyl iminium ions, reactions with allylic silanes      575
Acyl l,3-thiazoline-2-thiones, aldol addition reactions of      76 86
Acyl l,3-thiazoline-2-thiones, reaction with acyl iminium ions      100
Acyl oxazolinones, aldol addition reactions of      75 85Ч86
Acyl oxazolinones, enantioselective alkylation of      30Ч31
Acyl oxazolinones, in synthesis of Prelog Ч Djerassi lactone      876
Acyl oxazolinones, reactions with acyl iminium ions      100
Acylation of, alcohols      166Ч168 172
Acylation of, alkenes      597Ч598
Acylation of, amines      172Ч179
Acylation of, aromatic rings      704Ч710
Acylation of, ester enolates      102Ч105
Acylation of, ketone enolates      108Ч109
Acylium ions, in ene reactions      597Ч598
Acylium ions, in Friedel Ч Crafts acylation reactions      704Ч705
Acyloin condensation      305Ч306
Acyloins      see УKetones
Alane, in reduction of amides      271
Alcohols, acylation of      166Ч168 172 829Ч830
Alcohols, allylic, enantioselective epoxidation      760Ч764 880
Alcohols, allylic, from alkenes by selenium dioxide oxidation      805Ч806
Alcohols, allylic, from alkenes by singlet oxygen oxidation      783Ч786
Alcohols, allylic, from alkenes via selenides      806
Alcohols, allylic, from allylic selenides      395
Alcohols, allylic, from allylic sulfoxides by [2,3]-sigmatropic rearrangement      395
Alcohols, allylic, from epoxides by ring-opening      781Ч782
Alcohols, allylic, iodocyclization of monocarbonate esters of      206
Alcohols, allylic, oxidation by manganese dioxide      751
Alcohols, allylic, Sharpless epoxidation      762Ч764
Alcohols, allylic, titanium-catalyzed epoxidation      762Ч764
Alcohols, allylic, vanadium-catalyzed epoxidation      760Ч762
Alcohols, benzylic, oxidation by manganese dioxide      751
Alcohols, conversion to alkyl halides      142Ч147
Alcohols, enantioselective synthesis via organoboranes      237Ч238
Alcohols, in Friedel Ч Crafts alkylation      703
Alcohols, in radical cyclization reactions      656Ч657
Alcohols, inversion of configuration of      153Ч154
Alcohols, oxidation      747Ч757
Alcohols, oxidation, by chlorodimethylsulfonium salts      754Ч755
Alcohols, oxidation, by chromium(VI) reagents      747Ч751
Alcohols, oxidation, by Dess Ч Martin reagent      755
Alcohols, oxidation, by dimethylsulfoxide-based reagents      752Ч755
Alcohols, oxidation, by manganese dioxide      619
Alcohols, oxidation, by oxoammonium ions      756
Alcohols, oxidation, by potassium ferrate      751
Alcohols, oxidation, by ruthenium tetroxide      752
Alcohols, oxidation, to carboxylic acids      757
Alcohols, preparation from, aldehydes and ketones by Grignard addition      446Ч450
Alcohols, preparation from, aldehydes and ketones by reduction      262Ч265
Alcohols, preparation from, alkenes by hydroboration-oxidation      232Ч233 237Ч238
Alcohols, preparation from, alkenes by oxymercuration      196Ч199
Alcohols, preparation from, allylic boranes and aldehydes      559Ч563
Alcohols, preparation from, epoxides and organocopper reagents      487
Alcohols, preparation from, epoxides by reduction      284
Alcohols, preparation from, esters by Grignard addition      447
Alcohols, preparation from, esters by hydride reduction      265
Alcohols, preparation from, organoboranes by carbonylation      549
Alcohols, protecting groups for      822Ч831
Alcohols, reductive deoxygenation of      290
Aldehydes, $\alpha,\beta$-unsaturated, from aldol condensation      58Ч60
Aldehydes, $\alpha,\beta$-unsaturated, from alkenes by selenium dioxide oxidation      805Ч806
Aldehydes, $\alpha,\beta$-unsaturated, from alkenyl silanes      568
Aldehydes, $\alpha,\beta$-unsaturated, reactions with allylic silanes      576
Aldehydes, $\beta$-alkoxy, aldol condensation reactions of      84Ч85
Aldehydes, aldol addition and condensation of      57Ч94
Aldehydes, alkylation of      28
Aldehydes, aromatic, by formylation      710Ч711
Aldehydes, aromatic, by oxidation at methyl groups      807
Aldehydes, decarbonylation of      531
Aldehydes, oxidation of      796Ч796
Aldehydes, preparation from, alcohols by oxidation      747Ч751
Aldehydes, preparation from, alkenes by hydroformylation      529Ч530
Aldehydes, preparation from, alkenes by ozonolysis      788Ч790
Aldehydes, preparation from, alkenyl silanes by epoxidation      780
Aldehydes, preparation from, by reduction of nitriles      269
Aldehydes, preparation from, diols by oxidative cleavage      790Ч791
Aldehydes, preparation from, esters by partial reduction      268
Aldehydes, preparation from, from organoboranes by carbonylation      549Ч550 555
Aldehydes, preparation from, N-methoxy-N-methylamides      268Ч269
Aldehydes, preparation from, reaction of Grignard reagents with triethyl orthoformate      451
Aldehydes, protecting groups for      835Ч837
Aldehydes, reaction with, allylic boranes      559Ч563
Aldehydes, reaction with, allylic silanes      568Ч572
Aldehydes, reaction with, allylic stannanes      579Ч585
Aldehydes, reaction with, organomagnesium compounds      447
Aldehydes, reduction by, hydride donors      262Ч265
Aldehydes, reduction by, silanes      286Ч287
Aldehydes, unsaturated, cyclization by Lewis acids      598
Alder rule      334
Aldol addition and condensation      57Ч94
Aldol addition and condensation, cyclic transition state for      64Ч65
Aldol addition and condensation, enantioselectivity in      83Ч89
Aldol addition and condensation, intramolecular      89Ч95
Aldol addition and condensation, mechanism of      57Ч60
Aldol addition and condensation, mixed condensation with aromatic aldehydes      60Ч62
Aldol addition and condensation, of boron enolates      71Ч74
Aldol addition and condensation, of silyl enol ethers      78Ч82
Aldol addition and condensation, reversibility of      66Ч67
Aldol addition and condensation, stereoselectivity of      64Ч70 71Ч78
Alkenes, acylation of      597Ч598
Alkenes, addition of, alcohols      195
Alkenes, addition of, carbenes      625Ч634
Alkenes, addition of, halogens      200Ч209
Alkenes, addition of, hydrogen halides      191Ч195
Alkenes, addition of, radicals      651Ч652 657Ч660
Alkenes, addition of, selenium reagents      209Ч210 805Ч807
Alkenes, addition of, silanes      566Ч567
Alkenes, addition of, stannanes      576
Alkenes, addition of, sulfenyl halides      209Ч213
Alkenes, addition of, trifluoroacetic acid      195Ч196
Alkenes, arylation by diazonium ions      722
Alkenes, bromohydrins from      202Ч203
Alkenes, cycloaddition reactions with, azomethine ylides      366
Alkenes, cycloaddition reactions with, diazo compounds      360Ч362
Alkenes, cycloaddition reactions with, nitrile oxides      365
Alkenes, cycloaddition reactions with, nitrones      364Ч365
Alkenes, enantioselective      236Ч238
Alkenes, epoxidation      767Ч772
Alkenes, epoxidation, by dioxiranes      770Ч772
Alkenes, epoxidation, by nitriles and hydrogen peroxide      768
Alkenes, epoxidation, by peroxycarboxylic acids      767Ч768
Alkenes, epoxidation, enantioselective by Mn(salen) reagents      764Ч766
Alkenes, epoxidation, hydroxyl group directing effect      768
Alkenes, epoxidation, stereoselectivity of      768Ч769
Alkenes, hydration of      195
Alkenes, hydroboration of      226Ч231
Alkenes, hydroformylation      529Ч530
Alkenes, hydroformylation, hydrogenation of      249Ч260
Alkenes, in Friedel Ч Crafts alkylation      699
Alkenes, metal ion complexes of      531Ч532
Alkenes, oxidation by, chromium(VI) reagents, allylic      803Ч804
Alkenes, oxidation by, chromium(VI) reagents, cleavage      786Ч787
Alkenes, oxidation by, copper reagents, allylic      804
Alkenes, oxidation by, osmium tetroxide      758Ч760
Alkenes, oxidation by, osmium tetroxide-periodate      786
Alkenes, oxidation by, palladium-catalyzed      501
Alkenes, oxidation by, phenylselenenic acid      807
Alkenes, oxidation by, potassium permanganate      757Ч758 786
Alkenes, oxidation by, potassium permanganate-periodate      786
Alkenes, oxidation by, selenium dioxide      805Ч806
Alkenes, oxidation by, singlet oxygen      782Ч786
Alkenes, oxymercuration of      196Ч200
Alkenes, ozonolysis of      788Ч790
Alkenes, palladium-catalyzed carbonylation of      521
Alkenes, palladium-catalyzed oxidation      501
Alkenes, palladium-catalyzed reaction with aryl halides      503Ч507
Alkenes, photocycloaddition reactions of      370Ч376
Alkenes, preparation of, $\beta$-hydroxysilanes by elimination      120Ч121
Alkenes, preparation of, by alkylation of alkenyllithium reagents      445
Alkenes, preparation of, by reductive elimination      312Ч314
Alkenes, preparation of, by thermal elimination reactions      408Ч414
Alkenes, preparation of, by Wittig reactions      111Ч119
Alkenes, preparation of, carboxylic acids by oxidative decarboxylation      792
Alkenes, preparation of, dicarboxylic acids by bis-decarboxylation      793
Alkenes, preparation of, from alkenylboranes      556Ч559
Alkenes, preparation of, from alkynes by hydroboration      239Ч240
Alkenes, preparation of, from alkynes by reduction      260 284Ч286 295
Alkenes, preparation of, from carbonyl compounds by reductive dimerization      299 304Ч305
Alkenes, preparation of, from ketones by Lombardo's reagent      462
Alkenes, preparation of, sulfones by Ramberg Ч Baecklund rearrangement      611
Alkenes, reactivity in cycloaddition reactions      362
Alkylation, by conjugate addition reactions      39Ч45
Alkylation, Friedel Ч Crafts      699Ч705
Alkylation, of aldehydes      28
Alkylation, of carboxylic acid dianions      28
Alkylation, of dianions      20
Alkylation, of dihydro-l,3-oxazine anions      38Ч39
Alkylation, of enamines      33
Alkylation, of enol silyl ethers      596Ч597
Alkylation, of enolates      11Ч20
Alkylation, of enolates, intramolecular      19Ч20
Alkylation, of enolates, of aldehydes      28
Alkylation, of enolates, of cyclohexanone      17Ч18
Alkylation, of enolates, of decalone      18Ч19
Alkylation, of enolates, of esters      29Ч30
Alkylation, of enolates, of N-acyl oxazolidinones      30Ч31
Alkylation, of enolates, solvent effects in      20Ч23
Alkylation, of enolates, stereoselectivity of      17Ч19
Alkylation, of hydrazones      38Ч39
Alkylation, of imine anions      33Ч37
Alkylation, of nitriles      31
Alkylation, of oxazoline anions      39
Alkylation, of phenols      27Ч28Alkylation in
Alkynes, addition of hydrogen halides      223Ч234
Alkynes, alkylation by organoboranes      556Ч559
Alkynes, halogenation of      225Ч226
Alkynes, hydration of      224
Alkynes, oxidation of      758
Alkynes, palladium-catalyzed reaction with alkenyl halides      510
Alkynes, partial hydrogenation of      260
Alkynes, reactions with, organocopper reagents      495
Alkynes, reactions with, stannanes      576Ч578
Alkynes, reduction by, dissolving metals      295
Alkynes, reduction by, lithium aluminum hydride      284Ч286
Allenes, electrophilic addition to      222Ч223
Allenes, preparation from, cyclopropenylidenes      640
Allenes, preparation from, organocuprates and propargylic reagents      486
Amides, acetals, Claisen rearrangement of      392
Amides, alkylation of      156
Amides, chiral, iodocyclization of      207
Amides, lithiation of      441
Amides, N-bromo, Hofmann rearrangement      646Ч648
Amides, N-iodo, radical reactions of      655
Amides, N-methoxy-N-methyl, reaction with organolithium reagents      457
Amides, oxidation to carbamates      649
Amides, preparation, by acylation      172Ч179
Amides, preparation, by Claisen rearrangement of O-allylic amide acetals      392
Amides, preparation, from ketones by reaction with hydrazoic acid      649
Amides, preparation, from nitriles      179
Amides, preparation, from oximes by Beckmann rearrangement      650Ч651
Amides, protecting groups for      832Ч833
Amides, reduction, by alane      279
Amides, reduction, diborane      278Ч279
Amides, reduction, diisobutylaluminum hydride      279 834
Amides, reduction, lithium aluminum hydride      265
Amine oxides, allylic, [2,3]-sigmatropic rearrangement of      397
Amine oxides, oxidations of boranes by      233
Amine oxides, thermal elimination reactions of      408Ч109
Amines, alkylation of      155
Amines, aromatic, diazotization of      714Ч715
Amines, aromatic, ortho-alkylation of      397
Amines, enantioselective synthesis of      238 468
Amines, preparation from, amides      265 646Ч648
Amines, preparation from, carboxylic acids by Curtius rearrangement      646Ч648
Amines, preparation from, carboxylic acids by Schmidt reaction      649Ч650
Amines, preparation from, imines by reduction with sodium cyanoboro-hydride      269Ч270
Amines, preparation from, organoboranes      235
Amines, preparation from, phthalimide by alkylation      155Ч156
Amines, protecting groups for      831Ч835
Amines, reductive alkylation of      269Ч270 288
Amino acids, enantioselective synthesis of      255Ч259
Amino acids, esters, chelation-controlled Claisen rearrangement      392
Ammonium ylides, [2,3]-sigmatropic rearrangement of      395Ч397
Anilines      see УAmines aromaticФ
Anthracene, Diels Ч Alder reactions of      347 727
Antisynthetic transforms      846
Aromatic compounds, Birch reduction      293Ч294
Aromatic compounds, carbene addition reactions      634
Aromatic compounds, chromium tricarbonyl complexes of      534Ч535
Aromatic compounds, halogenation      695Ч699
Aromatic compounds, mercuration      711Ч713
Aromatic compounds, nitration      693Ч695
Aromatic compounds, nitrene addition reactions      644Ч645
Aromatic compounds, oxidation of substituents      807
Aromatic compounds, thallation      713Ч714
Aromatic substitution, by addition-elimination      722Ч724
1 2 3 4 5 6
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