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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
N-hydroxysuccinimide, in activation of carboxylic acids 175—176
N-hydroxysuccinimide, in peptide coupling 899
N-methylpyrrolidinone as solvent 21—22
Nickel, organo-, compounds 525—529
Nickel, organo-, compounds, -allyl complexes 526 532
Nickel, organo-, compounds, as intermediates in coupling halides and Grignard reagents 528—529
Nickel, organo-, compounds, coupling of halides and sulfonates by 526—529
Nickel, organo-, compounds, in coupling of aryl boronic acids 529
Nitration 693—696
Nitration, by acetyl nitrate 694
Nitration, by nitronium salts 694—695
Nitration, by ozone and nitrogen dioxide 695
Nitration, by trifluoroacetyl nitrate 694
Nitration, catalysis by lanthanide salts 694
Nitrenes 642—645
Nitrenes, alkyl, rearrangement of 644
Nitrenes, aryl, rearrangement of 644
Nitrenes, carboalkoxy 644—645
Nitrenes, from azides 642—644
Nitrenes, sulfonyl 645
Nitrenoid intermediate 616
Nitrile oxides, cycloaddition reactions 361 365
Nitriles, -unsaturated, addition of organocopper reagents to 489
Nitriles, -alkoxy, as acyl anion equivalents 839 853
Nitriles, -halo, reactions with organoboranes 556
Nitriles, alkylation 31
Nitriles, aromatic acylation by 711
Nitriles, conversion to primary amides 179
Nitriles, in epoxidation of alkenes 768
Nitriles, preparation of, by conjugate addition of cyanide 46
Nitriles, preparation of, by nucleophilic substitution 150
Nitriles, preparation of, from aryl halides 728
Nitriles, reaction with organomagnesium compounds 450
Nitriles, reduction to aldehydes 269
Nitrite esters, alkoxy radicals from 656—657
Nitrite esters, diazotization by 715
Nitroalkenes, as dienophiles 342
Nitroalkenes, conjugate addition reactions of 45
Nitrones, cycloaddition reactions 364—365
Nitrosyl chloride, as reagent 217
NMP see “N-methylpyrrolidinone”
Normant reagents 495
Olefin metathesis, in epothilone A synthesis 893—894 907
Olefin metathesis, in Prelog — Djerassi lactone synthesis 881
Oligonucleotides, solid phase synthesis 900—903
Orbital symmetry requirements for, 1,3-dipolar cycloaddition 359
Orbital symmetry requirements for, Diels — Alder reaction 332—333
Orbital symmetry requirements for, [2 + 2] cycloaddition 368
Organoboron compounds see “Boranes”
Organocadmium compounds see “Cadmium organo-”
Organocerium compounds see “Cerium organo-”
Organocopper compounds see “Copper organo-”
Organolithium compounds see “Lithium organo-”
Organomagnesium compounds see “Magnesium organo-”
Organomercury compounds see “Mercury organo-”
Organometallic compounds with -bonding 531—535
Organonickel compounds see “Nickel organo-”
Organopalladium see “Palladium organo-”
Organothallium compounds see “Thallium organo-”
Organotin compounds see “Stannanes”
Organozinc compounds see “Zinc organo-”
Ortho esters, as carboxylic acid protecting groups 834
Ortho esters, in Claisen rearrangement of allylic alcohols 384 388—389
Ortho esters, reaction with Grignard reagents 451
Osmium tetroxide 758—760 786
Oxalyl chloride, in preparation of acid chlorides 116
Oxalyl chloride, in Swern oxidation 753
Oxaphosphetane, as intermediates in Wittig reaction 111—112
Oxazaborolidines, as catalysts for enantioselective reduction 279—280
Oxaziridines, sulfonyl, in oxidation of enolates 797—798 882
Oxazolidinones see “Acyl oxazolidinones”
Oxazolines, alkylation of anions 38—39
Oxazolines, as carboxylic acid-protecting groups 837
Oxetanes, from alkene-carbonyl photocycloaddition 374—376
Oxime ethers, radical addition reactions 666—667
Oximes, Beckmann rearrangement of 650—651
Oxirenes, as intermediates in Wolff rearrangement 641—642
Oxonium ylides 637—639
Oxy-Cope rearrangement 382—383
Oxy-Cope rearrangement, anionic 382
Oxy-Cope rearrangement, in synthesis of juvabione 853—854
Oxygen, reaction with, enolates 800—802
Oxygen, reaction with, radical intermediates 198
Oxygen, singlet, generation of 782
Oxygen, singlet, lifetime of 782
Oxygen, singlet, reaction with alkenes 782—786
Oxymercuration 196—200
Oxymercuration, stereoselectivity of 200
Ozonolysis 788—790
Palladium, organo- compounds, -allyl, preparation of 499—500
Palladium, organo- compounds, -allyl, reaction with enolates 501—503
Palladium, organo- compounds, as reaction intermediates in 499—525
Palladium, organo- compounds, as reaction intermediates in, conversion of alkenyl halides to esters by carbonylation 521—525
Palladium, organo- compounds, as reaction intermediates in, coupling of alkynes and alkenyl halides 510
Palladium, organo- compounds, as reaction intermediates in, coupling of halides and organometallic reagents 507—510
Palladium, organo- compounds, as reaction intermediates in, nucleophilic aromatic substitution 730—731
Palladium, organo- compounds, as reaction intermediates in, oxidation of alkenes 501
Palladium, organo- compounds, as reaction intermediates in, reaction of aryl halides and alkenes 503—507
Palladium, organo- compounds, catalysis of cleavage of allylic carbamates and carbonates 830—832
Palladium, organo- compounds, catalysts for nucleophilic aromatic substitution 730—731
Palladium, organo- compounds, formation by oxidative addition 499 504 522
Paterno — Buchi reaction 374
Pericyclic reactions, definition 331
Periodate ion, cleavage of diols 786 790—791
Permanganate ion, oxidation of, alkenes 757—758
Permanganate ion, oxidation of, alkynes 758
Permanganate ion, oxidation of, aromatic side-chains 807
Peroxycarboxylic acids, epoxidation of alkenes 767—772
Peroxycarboxylic acids, oxidation of ketones 798—801
Peterson reaction 120—121
Phase transfer catalysis 149—150 505 623
Phenolate anions, C- versus O-alkylation of 27—28
Phenylselenenyl halides, as reagents 213—215
Phenylselenenyl sulfate, as reagent 214
Phosphate esters, alkenyl, reduction of 296
Phosphate esters, aryl, reduction of 296
Phosphines, as catalysts for O-acylation 168
Phosphines, as ligands in palladium catalysts 508 730
Phosphines, chiral, in hydrogenation catalysts 255—259
Phosphite esters, dialkyl, as hydrogen atom donors 290
Phosphite esters, preparation under Mitsunobu conditions 154—155
Phosphonate carbanions, Wittig reactions of 116—117
Phosphonate esters, preparation of 158—159
Phosphonium salts, alkoxy, as intermediates in nucleophilic substitution 144—145
Phosphonium salts, cyclopropyl, as synthetic equivalent groups 842—844
Phosphonium salts, deprotonation of 111
Phosphonium salts, preparation of 112
Phosphonium salts, vinyl, as dienophiles 343
Phosphoramidate method for nucleotide coupling 901
Phosphorus tribromide, in preparation of alkyl bromides 143—144
Phosphorus ylides 111—112
Phthalimide, as amine-protecting group 833
Phthalimide, in synthesis of amines 155—156
Pinacol borane, hydroboration by 229
Pinacol rearrangement 602—607
Pinacol rearrangement, in synthesis of longifolene 861—862
pK values for carbon acids 4
Polyene cyclization 598—602
Polypeptides, solid phase synthesis 987—900
Potassium ferrate 751
Prelog — Djerassi lactone, stereoselective synthesis of 869—881
Protective groups for 822—838
Protective groups for, amides, 2,4-dimethoxyphenyl 832
Protective groups for, amides, 4-methoxyphenyl 832
Protective groups for, amines 831—835
Protective groups for, amines, -trichloroethyloxycarbonyl 832
Protective groups for, amines, allyloxycarbonyl 831—832
Protective groups for, amines, amides as 834
Protective groups for, amines, carbobenzyloxy 831
Protective groups for, amines, o-nitrobenzyloxycarbonyl 832
Protective groups for, amines, phthalimides as 833
Protective groups for, amines, silyl derivatives 834
Protective groups for, amines, sulfonamides as 834
Protective groups for, amines, t-butoxycarbonyl 831
Protective groups for, amines, trifluoroacetyl 833
Protective groups for, carbonyl compounds 835—837
Protective groups for, carbonyl compounds, acetals 835
Protective groups for, carbonyl compounds, dioxolanes 835—836
Protective groups for, carbonyl compounds, dithioketals 836—837
Protective groups for, carbonyl compounds, oxathiolanes 836
Protective groups for, carboxylic acids 837—838
Protective groups for, carboxylic acids, -trichloroethyl esters 837
Protective groups for, carboxylic acids, ortho esters 838
Protective groups for, carboxylic acids, oxazolines 837
Protective groups for, carboxylic acids, t-butyl esters 837
Protective groups for, hydroxyl groups 822—831
Protective groups for, hydroxyl groups, -methoxyethoxymethyl 824
Protective groups for, hydroxyl groups, 1-ethoxyethyl 823
Protective groups for, hydroxyl groups, 3,5-dimethoxybenzyl 826
Protective groups for, hydroxyl groups, 4,4'-dimethoxytriphenylmethyl 900
Protective groups for, hydroxyl groups, 4-methoxybenzyl 826
Protective groups for, hydroxyl groups, allyl 827
Protective groups for, hydroxyl groups, allyoxycarbonyl 830
Protective groups for, hydroxyl groups, benzyl 825—827
Protective groups for, hydroxyl groups, cyanoethyl 901
Protective groups for, hydroxyl groups, methoxymethyl 824
Protective groups for, hydroxyl groups, methoxyphenyl 827
Protective groups for, hydroxyl groups, methylthiomethyl 824—825
Protective groups for, hydroxyl groups, silyl ethers 827—829
Protective groups for, hydroxyl groups, t-butyl 825
Protective groups for, hydroxyl groups, tetrahydropyranyl 823
Protective groups for, hydroxyl groups, trichloroethyl carbonate esters 825
Protective groups for, hydroxyl groups, triphenylmethyl 825
Pummerer reaction 824
Pyrazolines, conversion to cyclopropanes 362 406
Pyrazolines, from dipolar cycloaddition reactions 360—361 866—867
Pyridazines, Diels — Alder reactions of 407
Pyridine-2-thiol esters as acylating agents 170—171
Pyridine-2-thione, N-hydroxy esters, radicals from 653 675
Pyridines, 2-halo, nucleophilic substitution reactions of 724
Pyridines, as catalysts for acylation 166
Pyridinium chlorochromate 750
Pyridinium dichromate 750
Pyrones, Diels — Alder addition reactions of 348 868 883
Quinodimethanes, as Diels — Alder dienes 345—347
Quinodimethanes, from benzo[b]thiophene dioxides 404
Quinones, as dienophiles 339
Radicals, 5-hexenyl, cyclization of 198 283 435
Radicals, alkoxy 656 674 678—679
Radicals, aryl, from N-nitrosoacetanilides 733
Radicals, aryl, reactions of 731—734
Radicals, as intermediates 651—652 654—679
Radicals, as intermediates, in preparation of organomagnesium compounds 435
Radicals, cyclization of 198 283 435 660—674
Radicals, cyclization of, regioselectivity and stereoselectivity in 660—662 665
Radicals, fragmentation reactions of 674—679
Radicals, generation of 652—654
Radicals, generation of, by Mn(III) oxidation 551
Radicals, generation of, by reduction of organomercury compounds 196—198 654 659
Radicals, generation of, from halides 652—654
Radicals, generation of, from N-hydroxypyridine-2-thione esters 652—653
Radicals, generation of, from selenides 653 666
Radicals, generation of, from thiono esters 290 665
Radicals, in aromatic substitution 731—734
Radicals, intramolecular hydrogen abstraction by 654—657
Radicals, rearrangement reactions of 674—679
Radicals, substituent effects on reactivity 657—658
Radicals, trapping of, by alkenes 657 660—667
Radicals, trapping of, by oxygen 198
Ramberg — Baecklund rerrangement 611
Red-Al see “Sodium bis(2-methoxyethoxy)aluminum hydride”
Reduction, by hydride donors 262—273
Reduction, by hydride donors, stereoselectivity of 273—277
Reduction, dissolving metal 290—295
Reductive amination 269—270
Resolution, in enantioselective synthesis 847
Retrosynthetic analysis 845—846
Rhodium compounds, as catalyst for, carbenoid addition and insertion reactions 632—637
Rhodium compounds, as catalyst for, decarbonylation 431
Rhodium compounds, as catalyst for, Fischer — Tropsch process 530
Rhodium compounds, as catalyst for, homogeneous hydrogenation 253
Rhodium compounds, as catalyst for, hydroboration 229—230 232
Rhodium compounds, as catalyst for, hydroformylation 529—530
Rhodium compounds, as catalyst for, hydrosilation 567
Rhodium compounds, as catalyst for, isomerization of organoboranes 232
Rink linker in oligonucleotide synthesis 899
Robinson annulation reaction 89—95
Ruthenium catalysts for hydrogenation 255—256
Samarium diiodide, reduction by 298 304—305 887
Sandmeyer reaction 717
Schiff base see “Imines”
Schmidt reaction 649
Selectrides see “Trialkylborohydrides”
Selenenyl halides, addition reactions with alkenes 213—216 806
Selenides, preparation of 213—216 410
Selenides, preparation of, -halo, oxidative elimination of 806
Selenides, preparation of, -hydroxy, from epoxides 781
Selenium dioxide 802 805—806
Selenocyclization 213—214
Selenoxides, allylic, [2,3]-sigmatropic rearrangements of 395 806
Selenoxides, in conversion of alkenes to allylic alcohols 806—807
Selenoxides, in conversion of epoxides to allylic alcohols 781
Selenoxides, preparation from selenides 410
Selenoxides, thermal elimination reactions of 410
Shapiro reaction 309—310 444
Sharpless asymmetric epoxidation 762—764
Sharpless asymmetric epoxidation, in synthesis of Prelog — Djerassi lactone 878—880
Silanes, alkenyl, epoxidation and conversion to ketones 780
Silanes, alkenyl, reactions with electrophiles 567—568 596
Silanes, allylic, -hydroxy, elimination reactions of 120—121
Silanes, allylic, arylation by Heck reaction 505—507
Silanes, allylic, as hydride donors 286—287
Silanes, allylic, as hydrogen atom donors 290 314 658 664
Silanes, allylic, carbanions of 120—121
Silanes, allylic, in polyene cyclizations 600—601
Silanes, allylic, reaction with electrophiles 567—570 596
Silanes, allylic, reactions with -unsaturated carbonyl compounds 575—576
Silanes, allylic, synthesis of 563—567
Silyl enol ethers, aldol addition reactions of 78—82
Silyl enol ethers, alkylation of 596—597
Silyl enol ethers, conjugate addition of 41 45
Silyl enol ethers, conversion to -hydroxyketones by oxidation 779—780 797
Silyl enol ethers, enolates from 11
Silyl enol ethers, epoxidation and rearrangement of 780 797
Silyl enol ethers, halogenation of 219
Silyl enol ethers, in Mukaiyama reactions 78—82
Silyl enol ethers, of ester enolates, Claisen rearrangement of 389—390 874—876
Silyl enol ethers, of ester enolates, stereoselective formation 389
Silyl enol ethers, oxidation of 796—797
Silyl enol ethers, photochemical cycloaddition 376
Silyl enol ethers, preparation from trimethylsilyl esters and Lombardo's reagent 463
Silyl ketene acetals, Claisen rearrangement of 389—390
Simmons — Smith reagent 626
Sodium bis-(2-methoxyethoxy)aluminum hydride 266 268
Sodium borohydride 264—265
Sodium cyanoborohydride 266 269 307
Solid phase synthesis 897—903
Solvent effects, in enolate alkylation 20—23
Solvent effects, in nucleophilic substitution 147—150
Solvent effects, on Diels — Alder reactions 339
Solvents, polar aprotic 21
Stannaries, -alkoxy, preparation of 444 578—579
Stannaries, -alkoxy, reaction with organolithium compounds 444
Stannaries, -amino, preparation of 578
Stannaries, alkenyl, palladium-catalyzed coupling with alkenyl trifluoromethanesulfonates 515
Stannaries, alkenyl, palladium-catalyzed coupling with halides 511—515
Stannaries, alkenyl, reactions with carbocations 596
Stannaries, allylic, radical substitution reactions of 660
Stannaries, allylic, reactions with acetals 583
Stannaries, allylic, reactions with aldehydes 579—582
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