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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
-diones, cleavage by periodate 791
-diones, preparation by, oxidation of alkynes 758
-diones, preparation by, oxidation of enamino ketones 785
-diones, preparation by, oxidation of ketones by selenium dioxide 802
-diketones, alkylation of 13—14
-ketoacids, decarboxylation of 14
-allyl complexes, of nickel 532
-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, -unsaturated, from aldol condensation 58—60
Aldehydes, -unsaturated, from alkenes by selenium dioxide oxidation 805—806
Aldehydes, -unsaturated, from alkenyl silanes 568
Aldehydes, -unsaturated, reactions with allylic silanes 576
Aldehydes, -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, -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
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