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Organic Reaction Mechanisms [2004]

1
Level 1 — Case 1 A Surprise in the Synthesis of Guanacastepene A
1
Reactions of Aldehydes and Ketones and Their Derivatives
1
Reactions of Aldehydes and Ketones and Their Derivatives
7
Level 1 — Case 2 Sulfenylation of Indole
13
Level 1 — Case 3 Substrate Selective Reactions in the Presence of Lewis Acids
21
Level 1 — Case 4 Diastereoselective Reductions of β-Ketoesters
27
Level 1 — Case 5 Rearrangements from Tetrahydropyran Derivatives
33
Level 1 — Case 6 Stereospecific Substitution Reactions of Epoxy Sulfides
39
Level 1 — Case 7 NaBH<Subscript>4</Subscript> Reduction of α,β-Unsaturated Chromium Carbene Complexes
45
Reactions of Carboxylic, Phosphoric and Sulfonic Acids and Their Derivatives
47
Level 1 — Case 8 Addition of Hydroxylamines to α,β-Unsaturated Esters
49
Reactions of Carboxylic, Phosphoric, and Sulfonic Acids and Their Derivatives
55
Level 1 — Case 9 Solvolysis of Electron-Deficient Norbornyl Triflates
63
Level 1 — Case 10 Nucleophile Versus Base Catalysis
69
Level 1 — Case 11 The Hydrolysis of <Emphasis Type="Italic">p</Emphasis>-Substituted Styrene Oxides
79
Level 1 — Case 12 Elimination Reactions of Benzaldehyde <Emphasis Type="Italic">O</Emphasis>-Benzoyloximes
87
Level 1 — Case 13 Oxygen Versus Sulfur Stabilization of Carbenium Ions
97
Level 1 — Case 14 Cyclization of 2,3-Dibenzylidenesuccinates
101
Level 1 — Case 15 Oxazoline <Emphasis Type="Italic">N</Emphasis>-Oxides as Dipoles in [3+2] Cycloadditions
107
Level 1 — Case 16 Light-Induced Cycloadditions of <Emphasis Type="BoldItalic">N</Emphasis>-Phthaloyl α-Amino Acids
113
Level 2 — Case 17 Change in Rate-Determining Step in an E1cB Mechanism: Aminolysis of Sulfamate Esters
115
Radical Reactions: Part 1
119
Level 2 — Case 18 Unusual Diels-Alder Reactivity of Acyclic 2-Azadienes
125
Level 2 — Case 19 Chelate-Controlled Carbonyl Addition Reactions
125
Radical Reactions: Part 1
131
Level 2 — Case 20 Esterification of Carboxylic Acids with Dimethyl Carbonate and DBU
139
Level 2 — Case 21 A Hammett Analysis in a Multistep Reaction: Rhodium(II)-Catalyzed Decomposition of α-Diazo Esters
145
Level 2 — Case 22 Tandem Cycloadditions with Nitronates
149
Radical Reactions: Part 2
153
Level 2 — Case 23 Hydrolysis of 2-Aminobenzoate Esters
159
Level 2 — Case 24 Rearrangements of Cyclobutenones
163
Level 2 — Case 25 Epoxi Ester-Orthoester Rearrangement
163
Radical Reactions: Part 2
169
Level 2 — Case 26 2-Chloro-1,3,5-triazines as Activating Groups of Carboxylic Acids in the Formation of Peptide Bonds
177
Level 2 — Case 27 Acid-Catalyzed Isomerization of Imines
179
Oxidation and Reduction
183
Level 2 — Case 28 A Dearomatizing Disrotatory Electrocyclic Ring Closure
189
Level 2 — Case 29 Stereoselective Debromination of Vicinal Dibromides
197
Level 2 — Case 30 Diels-Alder Reactions of <Emphasis Type="Italic">N</Emphasis>-Acyl-1,2,4,5-tetrazines
203
Level 2 — Case 31 Stereoselective Synthesis of 2-Acylaziridines
203
Oxidation and Reduction
209
Carbenes and Nitrenes
211
Level 3 - Case 32 The Baylis-Hillman Reaction
217
Level 3 - Case 33 The Rate-Determining Step in the S<Subscript>N</Subscript>Ar Reaction
225
Level 3 - Case 34 Helicenophanes and their Racemization
229
Nucleophilic Aromatic Substitution
231
Level 3 - Case 35 Solvolysis of Vinyl Iodonium Salts
237
Level 3 - Case 36 Vicarious Nucleophilic Substitution
239
Electrophilic Aromatic Substitution
243
Level 3 - Case 37 Base-promoted HF Elimination from 4-Fluoro-4-(4’nitrophenyl)butan-2-one
249
Carbocations
251
Level 3 - Case 38 Substitution of β-Halostyrenes by MeS<Superscript>-</Superscript>
259
Carbenes and Nitrenes
259
Level 3 - Case 39 Periodinane-Mediated Cyclization of Anilides
269
Level 3 - Case 40 Solvolysis of 8-Deltacyclyl Brosylates
277
Nucleophilic Aliphatic Substitution
283
Nucleophilic Aromatic Substitution
295
Electrophilic Aromatic Substitution
305
Carbocations
307
Carbanions and Electrophilic Aliphatic Substitution
341
Nucleophilic Aliphatic Substitution
351
Elimination Reactions
373
Carbanions and Electrophilic Aliphatic Substitution
375
Addition Reactions: Polar Addition
413
Elimination Reactions
427
Addition Reactions: Cycloaddition
443
Addition Reactions: Polar Addition
475
Molecular Rearrangements
499
Addition Reactions: Cycloaddition
553
Molecular Rearrangements
601
Author Index
643
Subject Index
669
Author Index
711
Subject Index
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Front Matter
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Front Matter
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