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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
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, $\pi$-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, $\alpa,\beta$-unsaturated, addition of organocopper reagents to      489
Nitriles, $\alpha$-alkoxy, as acyl anion equivalents      839 853
Nitriles, $\alpha$-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 $\pi$-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, $\pi$-allyl, preparation of      499—500
Palladium, organo- compounds, $\pi$-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, $\beta,\beta,\beta$-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, $\beta,\beta,\beta$-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, $\beta$-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, $\beta$-halo, oxidative elimination of      806
Selenides, preparation of, $\beta$-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, $\beta$-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 $\alpha,\beta$-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 $\alpha$-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, $\alpha$-alkoxy, preparation of      444 578—579
Stannaries, $\alpha$-alkoxy, reaction with organolithium compounds      444
Stannaries, $\alpha$-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
1 2 3 4 5 6
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