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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
$\alpha$-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      13—14
$\beta$-ketoacids, decarboxylation of      14
$\pi$-allyl complexes, of nickel      532
$\pi$-allyl complexes, of palladium      499—500 532
1,2-diols, cleavage by, lead tetraacetate      791
1,2-diols, cleavage by, periodate      757 790—791
1,2-diols, monotosylates, rearrangement of      604—607
1,2-diols, preparation by, epoxide ring-opening      772—774
1,2-diols, preparation by, hydroxylation of alkenes      757—760
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      602—607
1,2-diols, reductive deoxygention      312—314
1,3-diols, fragmentation of      613—614
1,3-dipoles      359
1,5-dienes, hydroboration of      871
1,5-dienes, [3,3]-sigmatropic rearrangements of      376—382
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      169—170
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      572—573
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      23—25
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      839—841
Acyl imidazolides, acylation of carbanion by      107
Acyl imidazolides, ester formation by      168—169 829—830
Acyl iminium ions, addition reactions of      99—100
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 85—86
Acyl oxazolinones, enantioselective alkylation of      30—31
Acyl oxazolinones, in synthesis of Prelog — Djerassi lactone      876
Acyl oxazolinones, reactions with acyl iminium ions      100
Acylation of, alcohols      166—168 172
Acylation of, alkenes      597—598
Acylation of, amines      172—179
Acylation of, aromatic rings      704—710
Acylation of, ester enolates      102—105
Acylation of, ketone enolates      108—109
Acylium ions, in ene reactions      597—598
Acylium ions, in Friedel — Crafts acylation reactions      704—705
Acyloin condensation      305—306
Acyloins      see “Ketones
Alane, in reduction of amides      271
Alcohols, acylation of      166—168 172 829—830
Alcohols, allylic, enantioselective epoxidation      760—764 880
Alcohols, allylic, from alkenes by selenium dioxide oxidation      805—806
Alcohols, allylic, from alkenes by singlet oxygen oxidation      783—786
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      781—782
Alcohols, allylic, iodocyclization of monocarbonate esters of      206
Alcohols, allylic, oxidation by manganese dioxide      751
Alcohols, allylic, Sharpless epoxidation      762—764
Alcohols, allylic, titanium-catalyzed epoxidation      762—764
Alcohols, allylic, vanadium-catalyzed epoxidation      760—762
Alcohols, benzylic, oxidation by manganese dioxide      751
Alcohols, conversion to alkyl halides      142—147
Alcohols, enantioselective synthesis via organoboranes      237—238
Alcohols, in Friedel — Crafts alkylation      703
Alcohols, in radical cyclization reactions      656—657
Alcohols, inversion of configuration of      153—154
Alcohols, oxidation      747—757
Alcohols, oxidation, by chlorodimethylsulfonium salts      754—755
Alcohols, oxidation, by chromium(VI) reagents      747—751
Alcohols, oxidation, by Dess — Martin reagent      755
Alcohols, oxidation, by dimethylsulfoxide-based reagents      752—755
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      446—450
Alcohols, preparation from, aldehydes and ketones by reduction      262—265
Alcohols, preparation from, alkenes by hydroboration-oxidation      232—233 237—238
Alcohols, preparation from, alkenes by oxymercuration      196—199
Alcohols, preparation from, allylic boranes and aldehydes      559—563
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      822—831
Alcohols, reductive deoxygenation of      290
Aldehydes, $\alpha,\beta$-unsaturated, from aldol condensation      58—60
Aldehydes, $\alpha,\beta$-unsaturated, from alkenes by selenium dioxide oxidation      805—806
Aldehydes, $\alpha,\beta$-unsaturated, from alkenyl silanes      568
Aldehydes, $\alpha,\beta$-unsaturated, reactions with allylic silanes      576
Aldehydes, $\beta$-alkoxy, aldol condensation reactions of      84—85
Aldehydes, aldol addition and condensation of      57—94
Aldehydes, alkylation of      28
Aldehydes, aromatic, by formylation      710—711
Aldehydes, aromatic, by oxidation at methyl groups      807
Aldehydes, decarbonylation of      531
Aldehydes, oxidation of      796—796
Aldehydes, preparation from, alcohols by oxidation      747—751
Aldehydes, preparation from, alkenes by hydroformylation      529—530
Aldehydes, preparation from, alkenes by ozonolysis      788—790
Aldehydes, preparation from, alkenyl silanes by epoxidation      780
Aldehydes, preparation from, by reduction of nitriles      269
Aldehydes, preparation from, diols by oxidative cleavage      790—791
Aldehydes, preparation from, esters by partial reduction      268
Aldehydes, preparation from, from organoboranes by carbonylation      549—550 555
Aldehydes, preparation from, N-methoxy-N-methylamides      268—269
Aldehydes, preparation from, reaction of Grignard reagents with triethyl orthoformate      451
Aldehydes, protecting groups for      835—837
Aldehydes, reaction with, allylic boranes      559—563
Aldehydes, reaction with, allylic silanes      568—572
Aldehydes, reaction with, allylic stannanes      579—585
Aldehydes, reaction with, organomagnesium compounds      447
Aldehydes, reduction by, hydride donors      262—265
Aldehydes, reduction by, silanes      286—287
Aldehydes, unsaturated, cyclization by Lewis acids      598
Alder rule      334
Aldol addition and condensation      57—94
Aldol addition and condensation, cyclic transition state for      64—65
Aldol addition and condensation, enantioselectivity in      83—89
Aldol addition and condensation, intramolecular      89—95
Aldol addition and condensation, mechanism of      57—60
Aldol addition and condensation, mixed condensation with aromatic aldehydes      60—62
Aldol addition and condensation, of boron enolates      71—74
Aldol addition and condensation, of silyl enol ethers      78—82
Aldol addition and condensation, reversibility of      66—67
Aldol addition and condensation, stereoselectivity of      64—70 71—78
Alkenes, acylation of      597—598
Alkenes, addition of, alcohols      195
Alkenes, addition of, carbenes      625—634
Alkenes, addition of, halogens      200—209
Alkenes, addition of, hydrogen halides      191—195
Alkenes, addition of, radicals      651—652 657—660
Alkenes, addition of, selenium reagents      209—210 805—807
Alkenes, addition of, silanes      566—567
Alkenes, addition of, stannanes      576
Alkenes, addition of, sulfenyl halides      209—213
Alkenes, addition of, trifluoroacetic acid      195—196
Alkenes, arylation by diazonium ions      722
Alkenes, bromohydrins from      202—203
Alkenes, cycloaddition reactions with, azomethine ylides      366
Alkenes, cycloaddition reactions with, diazo compounds      360—362
Alkenes, cycloaddition reactions with, nitrile oxides      365
Alkenes, cycloaddition reactions with, nitrones      364—365
Alkenes, enantioselective      236—238
Alkenes, epoxidation      767—772
Alkenes, epoxidation, by dioxiranes      770—772
Alkenes, epoxidation, by nitriles and hydrogen peroxide      768
Alkenes, epoxidation, by peroxycarboxylic acids      767—768
Alkenes, epoxidation, enantioselective by Mn(salen) reagents      764—766
Alkenes, epoxidation, hydroxyl group directing effect      768
Alkenes, epoxidation, stereoselectivity of      768—769
Alkenes, hydration of      195
Alkenes, hydroboration of      226—231
Alkenes, hydroformylation      529—530
Alkenes, hydroformylation, hydrogenation of      249—260
Alkenes, in Friedel — Crafts alkylation      699
Alkenes, metal ion complexes of      531—532
Alkenes, oxidation by, chromium(VI) reagents, allylic      803—804
Alkenes, oxidation by, chromium(VI) reagents, cleavage      786—787
Alkenes, oxidation by, copper reagents, allylic      804
Alkenes, oxidation by, osmium tetroxide      758—760
Alkenes, oxidation by, osmium tetroxide-periodate      786
Alkenes, oxidation by, palladium-catalyzed      501
Alkenes, oxidation by, phenylselenenic acid      807
Alkenes, oxidation by, potassium permanganate      757—758 786
Alkenes, oxidation by, potassium permanganate-periodate      786
Alkenes, oxidation by, selenium dioxide      805—806
Alkenes, oxidation by, singlet oxygen      782—786
Alkenes, oxymercuration of      196—200
Alkenes, ozonolysis of      788—790
Alkenes, palladium-catalyzed carbonylation of      521
Alkenes, palladium-catalyzed oxidation      501
Alkenes, palladium-catalyzed reaction with aryl halides      503—507
Alkenes, photocycloaddition reactions of      370—376
Alkenes, preparation of, $\beta$-hydroxysilanes by elimination      120—121
Alkenes, preparation of, by alkylation of alkenyllithium reagents      445
Alkenes, preparation of, by reductive elimination      312—314
Alkenes, preparation of, by thermal elimination reactions      408—414
Alkenes, preparation of, by Wittig reactions      111—119
Alkenes, preparation of, carboxylic acids by oxidative decarboxylation      792
Alkenes, preparation of, dicarboxylic acids by bis-decarboxylation      793
Alkenes, preparation of, from alkenylboranes      556—559
Alkenes, preparation of, from alkynes by hydroboration      239—240
Alkenes, preparation of, from alkynes by reduction      260 284—286 295
Alkenes, preparation of, from carbonyl compounds by reductive dimerization      299 304—305
Alkenes, preparation of, from ketones by Lombardo's reagent      462
Alkenes, preparation of, sulfones by Ramberg — Baecklund rearrangement      611
Alkenes, reactivity in cycloaddition reactions      362
Alkylation, by conjugate addition reactions      39—45
Alkylation, Friedel — Crafts      699—705
Alkylation, of aldehydes      28
Alkylation, of carboxylic acid dianions      28
Alkylation, of dianions      20
Alkylation, of dihydro-l,3-oxazine anions      38—39
Alkylation, of enamines      33
Alkylation, of enol silyl ethers      596—597
Alkylation, of enolates      11—20
Alkylation, of enolates, intramolecular      19—20
Alkylation, of enolates, of aldehydes      28
Alkylation, of enolates, of cyclohexanone      17—18
Alkylation, of enolates, of decalone      18—19
Alkylation, of enolates, of esters      29—30
Alkylation, of enolates, of N-acyl oxazolidinones      30—31
Alkylation, of enolates, solvent effects in      20—23
Alkylation, of enolates, stereoselectivity of      17—19
Alkylation, of hydrazones      38—39
Alkylation, of imine anions      33—37
Alkylation, of nitriles      31
Alkylation, of oxazoline anions      39
Alkylation, of phenols      27—28Alkylation in
Alkynes, addition of hydrogen halides      223—234
Alkynes, alkylation by organoboranes      556—559
Alkynes, halogenation of      225—226
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      576—578
Alkynes, reduction by, dissolving metals      295
Alkynes, reduction by, lithium aluminum hydride      284—286
Allenes, electrophilic addition to      222—223
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      646—648
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      172—179
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      650—651
Amides, protecting groups for      832—833
Amides, reduction, by alane      279
Amides, reduction, diborane      278—279
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      408—109
Amines, alkylation of      155
Amines, aromatic, diazotization of      714—715
Amines, aromatic, ortho-alkylation of      397
Amines, enantioselective synthesis of      238 468
Amines, preparation from, amides      265 646—648
Amines, preparation from, carboxylic acids by Curtius rearrangement      646—648
Amines, preparation from, carboxylic acids by Schmidt reaction      649—650
Amines, preparation from, imines by reduction with sodium cyanoboro-hydride      269—270
Amines, preparation from, organoboranes      235
Amines, preparation from, phthalimide by alkylation      155—156
Amines, protecting groups for      831—835
Amines, reductive alkylation of      269—270 288
Amino acids, enantioselective synthesis of      255—259
Amino acids, esters, chelation-controlled Claisen rearrangement      392
Ammonium ylides, [2,3]-sigmatropic rearrangement of      395—397
Anilines      see “Amines aromatic”
Anthracene, Diels — Alder reactions of      347 727
Antisynthetic transforms      846
Aromatic compounds, Birch reduction      293—294
Aromatic compounds, carbene addition reactions      634
Aromatic compounds, chromium tricarbonyl complexes of      534—535
Aromatic compounds, halogenation      695—699
Aromatic compounds, mercuration      711—713
Aromatic compounds, nitration      693—695
Aromatic compounds, nitrene addition reactions      644—645
Aromatic compounds, oxidation of substituents      807
Aromatic compounds, thallation      713—714
Aromatic substitution, by addition-elimination      722—724
1 2 3 4 5 6
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