Advanced Organic Chemistry: Reaction and Synthesis

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  • Edition: 4th
  • Format: Paperback
  • Copyright: 2001-07-01
  • Publisher: Springer Verlag
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The control of reactivity to achieve specific syntheses is one of the overarching goals of organic chemistry. In the decade since the publication of the third edition, major advances have been made in the development of efficient new methods, particularly catalytic processes, and in means for control of reaction stereochemistry. This volume assumes a level of familiarity with structural and mechanistic concepts comparable to that in the companion volume, Part A, Structures and Mechanisms . Together, the two volumes are intended to provide the advanced undergraduate or beginning graduate student in chemistry with a sufficient foundation to comprehend and use the research literature in organic chemistry. The New Revised 5th Edition will be available shortly. For details, click on the link in the right-hand column.

Table of Contents

Alkylation of Nucleophilic Carbon Intermediatesp. 1
Generation of Carbanions by Deprotonationp. 1
Regioselectivity and Stereoselectivity in Enolate Formationp. 5
Other Means of Generating Enolatesp. 10
Alkylation of Enolatesp. 11
Generation and Alkylation of Dianionsp. 20
Medium Effects in the Alkylation of Enolatesp. 20
Oxygen versus Carbon as the Site of Alkylationp. 23
Alkylation of Aldehydes, Esters, Amides, and Nitrilesp. 28
The Nitrogen Analogs of Enols and Enolates--Enamines and Imine Anionsp. 31
Alkylation of Carbon Nucleophiles by Conjugate Additionp. 39
General Referencesp. 47
Problemsp. 47
Reaction of Carbon Nucleophiles with Carbonyl Groupsp. 57
Aldol Addition and Condensation Reactionsp. 57
The General Mechanismp. 57
Mixed Aldol Condensations with Aromatic Aldehydesp. 60
Control of Regiochemistry and Stereochemistry of Mixed Aldol Reactions of Aliphatic Aldehydes and Ketonesp. 62
Intramolecular Aldol Reactions and the Robinson Annulationp. 89
Addition Reactions of Imines and Iminium Ionsp. 96
The Mannich Reactionp. 96
Amine-Catalyzed Condensation Reactionsp. 100
Acylation of Carbanionsp. 101
The Wittig and Related Reactions of Phosphorus-Stabilized Carbon Nucleophilesp. 111
Reactions of Carbonyl Compounds with [alpha]-Trimethylsilylcarbanionsp. 120
Sulfur Ylides and Related Nucleophilesp. 122
Nucleophilic Addition--Cyclizationp. 127
General Referencesp. 128
Problemsp. 128
Functional Group Interconversion by Nucleophilic Substitutionp. 141
Conversion of Alcohols to Alkylating Agentsp. 141
Sulfonate Estersp. 141
Halidesp. 142
Introduction of Functional Groups by Nucleophilic Substitution at Saturated Carbonp. 147
General Solvent Effectsp. 147
Nitrilesp. 150
Azidesp. 150
Oxygen Nucleophilesp. 152
Nitrogen Nucleophilesp. 155
Sulfur Nucleophilesp. 158
Phosphorus Nucleophilesp. 158
Summary of Nucleophilic Substitution at Saturated Carbonp. 159
Nucleophilic Cleavage of Carbon-Oxygen Bonds in Ethers and Estersp. 159
Interconversion of Carboxylic Acid Derivativesp. 164
Preparation of Reactive Reagents for Acylationp. 166
Preparation of Estersp. 172
Preparation of Amidesp. 172
Problemsp. 180
Electrophilic Additions to Carbon--Carbon Multiple Bondsp. 191
Addition of Hydrogen Halidesp. 191
Hydration and Other Acid-Catalyzed Additions of Oxygen Nucleophilesp. 195
Oxymercurationp. 196
Addition of Halogens to Alkenesp. 200
Electrophilic Sulfur and Selenium Reagentsp. 209
Addition of Other Electrophilic Reagentsp. 216
Electrophilic Substitution Alpha to Carbonyl Groupsp. 216
Additions to Allenes and Alkynesp. 222
Addition at Double Bonds via Organoborane Intermediatesp. 226
Hydroborationp. 226
Reactions of Organoboranesp. 232
Enantioselective Hydroborationp. 236
Hydroboration of Alkynesp. 239
General Referencesp. 240
Problemsp. 241
Reduction of Carbonyl and Other Functional Groupsp. 249
Addition of Hydrogenp. 249
Catalytic Hydrogenationp. 249
Other Hydrogen-Transfer Reagentsp. 262
Group III Hydride-Donor Reagentsp. 262
Reduction of Carbonyl Compoundsp. 262
Stereoselectivity of Hydride Reductionp. 273
Reduction of Other Functional Groups by Hydride Donorsp. 280
Group IV Hydride Donorsp. 286
Hydrogen-Atom Donorsp. 288
Dissolving-Metal Reductionsp. 290
Addition of Hydrogenp. 292
Reductive Removal of Functional Groupsp. 296
Reductive Carbon--Carbon Bond Formationp. 299
Reductive Deoxygenation of Carbonyl Groupsp. 307
Reductive Elimination and Fragmentationp. 310
General Referencesp. 315
Problemsp. 316
Cycloadditions, Unimolecular Rearrangements, and Thermal Eliminationsp. 331
Cycloaddition Reactionsp. 331
The Diels--Alder Reaction: General Featuresp. 332
The Diels--Alder Reaction: Dienophilesp. 339
The Diels--Alder Reaction: Dienesp. 345
Asymmetric Diels--Alder Reactionsp. 349
Intramolecular Diels--Alder Reactionsp. 353
Dipolar Cycloaddition Reactionsp. 359
[2 + 2] Cycloadditions and Other Reactions Leading to Cyclobutanesp. 367
Photochemical Cycloaddition Reactionsp. 370
[3,3] Sigmatropic Rearrangementsp. 376
Cope Rearrangementsp. 376
Claisen Rearrangementsp. 383
[2,3] Sigmatropic Rearrangementsp. 394
Ene Reactionsp. 399
Unimolecular Thermal Elimination Reactionsp. 403
Cheletropic Eliminationp. 403
Decomposition of Cyclic Azo Compoundsp. 405
[beta] Eliminations Involving Cyclic Transition Statesp. 408
General Referencesp. 414
Problemsp. 414
Organometallic Compounds of the Group I, II, and III Metalsp. 433
Preparation and Propertiesp. 433
Reactions of Organomagnesium and Organolithium Compoundsp. 445
Reactions with Alkylating Agentsp. 445
Reactions with Carbonyl Compoundsp. 446
Organic Derivatives of Group IIB and Group IIIB Metalsp. 458
Organozinc Compoundsp. 459
Organocadmium Compoundsp. 463
Organomercury Compoundsp. 464
Organoindium Reagentsp. 465
Organolanthanide Reagentsp. 467
General Referencesp. 468
Problemsp. 468
Reactions Involving the Transition Metalsp. 477
Organocopper Intermediatesp. 477
Preparation and Structure of Organocopper Reagentsp. 477
Reactions Involving Organocopper Reagents and Intermediatesp. 481
Reactions Involving Organopalladium Intermediatesp. 499
Palladium-Catalyzed Nucleophilic Substitution and Alkylationp. 501
The Heck Reactionp. 503
Palladium-Catalyzed Cross Couplingp. 507
Carbonylation Reactionsp. 521
Reactions Involving Organonickel Compoundsp. 525
Reactions Involving Rhodium and Cobaltp. 529
Organometallic Compounds with [pi] Bondingp. 531
General Referencesp. 535
Problemsp. 536
Carbon--Carbon Bond-Forming Reactions of Compounds of Boron, Silicon, and Tinp. 547
Organoboron Compoundsp. 547
Synthesis of Organoboranesp. 547
Carbon--Carbon Bond-Forming Reactions of Organoboranesp. 549
Organosilicon Compoundsp. 563
Synthesis of Organosilanesp. 563
Carbon--Carbon Bond-Forming Reactionsp. 567
Organotin Compoundsp. 576
Synthesis of Organostannanesp. 576
Carbon--Carbon Bond-Forming Reactionsp. 579
General Referencesp. 585
Problemsp. 586
Reactions Involving Carbocations, Carbenes, and Radicals as Reactive Intermediatesp. 595
Reactions Involving Carbocation Intermediatesp. 595
Carbon-Carbon Bond Formation Involving Carbocationsp. 596
Rearrangement of Carbocationsp. 602
Related Rearrangementsp. 609
Fragmentation Reactionsp. 612
Reactions Involving Carbenes and Nitrenesp. 614
Structure and Reactivity of Carbenesp. 617
Generation of Carbenesp. 620
Addition Reactionsp. 625
Insertion Reactionsp. 634
Generation and Reactions of Ylides by Carbenoid Decompositionp. 637
Rearrangement Reactionsp. 639
Related Reactionsp. 641
Nitrenes and Related Intermediatesp. 642
Rearrangements to Electron-Deficient Nitrogenp. 646
Reactions Involving Free-Radical Intermediatesp. 651
Sources of Radical Intermediatesp. 652
Introduction of Functionality by Radical Reactionsp. 654
Addition Reactions of Radicals to Substituted Alkenesp. 657
Cyclization of Free-Radical Intermediatesp. 660
Fragmentation and Rearrangement Reactionsp. 674
General Referencesp. 679
Problemsp. 680
Aromatic Substitution Reactionsp. 693
Electrophilic Aromatic Substitutionp. 693
Nitrationp. 693
Halogenationp. 695
Friedel-Crafts Alkylations and Acylationsp. 699
Electrophilic Metalationp. 711
Nucleophilic Aromatic Substitutionp. 714
Aryl Diazonium Ions as Synthetic Intermediatesp. 714
Substitution by the Addition-Elimination Mechanismp. 722
Substitution by the Elimination-Addition Mechanismp. 724
Transition-Metal-Catalyzed Substitution Reactionsp. 728
Aromatic Radical Substitution Reactionsp. 731
Substitution by the S[subscript RN]1 Mechanismp. 734
General Referencesp. 736
Problemsp. 736
Oxidationsp. 747
Oxidation of Alcohols to Aldehydes, Ketones, or Carboxylic Acidsp. 747
Transition-Metal Oxidantsp. 747
Other Oxidantsp. 752
Addition of Oxygen at Carbon-Carbon Double Bondsp. 757
Transition-Metal Oxidantsp. 757
Epoxides from Alkenes and Peroxidic Reagentsp. 767
Transformations of Epoxidesp. 772
Reaction of Alkenes with Singlet Oxygenp. 782
Cleavage of Carbon-Carbon Double Bondsp. 786
Transition-Metal Oxidantsp. 786
Oxonolysisp. 788
Selective Oxidative Cleavages at Other Functional Groupsp. 790
Cleavage of Glycolsp. 790
Oxidative Decarboxylationp. 792
Oxidation of Ketones and Aldehydesp. 794
Transition-Metal Oxidantsp. 794
Oxidation of Ketones and Aldehydes by Oxygen and Peroxidic Compoundsp. 798
Oxidation with Other Reagentsp. 802
Allylic Oxidationp. 803
Transition-Metal Oxidantsp. 803
Other Oxidantsp. 805
Oxidations at Unfunctionalized Carbonp. 807
General Referencesp. 809
Problemsp. 809
Planning and Execution of Multistep Synthesesp. 821
Protective Groupsp. 822
Hydroxyl-Protecting Groupsp. 822
Amino-Protecting Groupsp. 831
Carbonyl-Protecting Groupsp. 835
Carboxylic Acid-Protecting Groupsp. 837
Synthetic Equivalent Groupsp. 839
Synthetic Analysis and Planningp. 845
Control of Stereochemistryp. 846
Illustrative Synthesesp. 848
Juvabionep. 848
Longifolenep. 859
Prelog-Djerassi Lactonep. 869
Taxolp. 881
Epothilone Ap. 890
Solid-Phase Synthesisp. 897
Solid-Phase Synthesis of Polypeptidesp. 897
Solid-Phase Synthesis of Oligonucleotidesp. 900
Combinatorial Synthesisp. 903
General Referencesp. 909
Problemsp. 910
References for Problemsp. 923
Indexp. 947
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