Organic Reaction Mechanisms: 40 Solved Cases

Front Matter....Pages I-X
Level 1 — Case 1 A Surprise in the Synthesis of Guanacastepene A....Pages 1-6
Level 1 — Case 2 Sulfenylation of Indole....Pages 7-12
Level 1 — Case 3 Substrate Selective Reactions in the Presence of Lewis Acids....Pages 13-20
Level 1 — Case 4 Diastereoselective Reductions of β-Ketoesters....Pages 21-26
Level 1 — Case 5 Rearrangements from Tetrahydropyran Derivatives....Pages 27-32
Level 1 — Case 6 Stereospecific Substitution Reactions of Epoxy Sulfides....Pages 33-37
Level 1 — Case 7 NaBH 4 Reduction of α,β-Unsaturated Chromium Carbene Complexes....Pages 39-45
Level 1 — Case 8 Addition of Hydroxylamines to α,β-Unsaturated Esters....Pages 47-54
Level 1 — Case 9 Solvolysis of Electron-Deficient Norbornyl Triflates....Pages 55-62
Level 1 — Case 10 Nucleophile Versus Base Catalysis....Pages 63-68
Level 1 — Case 11 The Hydrolysis of p -Substituted Styrene Oxides....Pages 69-77
Level 1 — Case 12 Elimination Reactions of Benzaldehyde O -Benzoyloximes....Pages 79-86
Level 1 — Case 13 Oxygen Versus Sulfur Stabilization of Carbenium Ions....Pages 87-95
Level 1 — Case 14 Cyclization of 2,3-Dibenzylidenesuccinates....Pages 97-100
Level 1 — Case 15 Oxazoline N -Oxides as Dipoles in [3+2] Cycloadditions....Pages 101-106
Level 1 — Case 16 Light-Induced Cycloadditions of N -Phthaloyl α-Amino Acids....Pages 107-111
Level 2 — Case 17 Change in Rate-Determining Step in an E1cB Mechanism: Aminolysis of Sulfamate Esters....Pages 113-118
Level 2 — Case 18 Unusual Diels-Alder Reactivity of Acyclic 2-Azadienes....Pages 119-124
Level 2 — Case 19 Chelate-Controlled Carbonyl Addition Reactions....Pages 125-130
Level 2 — Case 20 Esterification of Carboxylic Acids with Dimethyl Carbonate and DBU....Pages 131-137
Level 2 — Case 21 A Hammett Analysis in a Multistep Reaction: Rhodium(II)-Catalyzed Decomposition of α-Diazo Esters....Pages 139-144
Level 2 — Case 22 Tandem Cycloadditions with Nitronates....Pages 145-151
Level 2 — Case 23 Hydrolysis of 2-Aminobenzoate Esters....Pages 153-157
Level 2 — Case 24 Rearrangements of Cyclobutenones....Pages 159-162
Level 2 — Case 25 Epoxi Ester-Orthoester Rearrangement....Pages 163-167
Level 2 — Case 26 2-Chloro-1,3,5-triazines as Activating Groups of Carboxylic Acids in the Formation of Peptide Bonds....Pages 169-175
Level 2 — Case 27 Acid-Catalyzed Isomerization of Imines....Pages 177-182
Level 2 — Case 28 A Dearomatizing Disrotatory Electrocyclic Ring Closure....Pages 183-188
Level 2 — Case 29 Stereoselective Debromination of Vicinal Dibromides....Pages 189-196
Level 2 — Case 30 Diels-Alder Reactions of N -Acyl-1,2,4,5-tetrazines....Pages 197-202
Level 2 — Case 31 Stereoselective Synthesis of 2-Acylaziridines....Pages 203-209
Level 3 - Case 32 The Baylis-Hillman Reaction....Pages 211-216
Level 3 - Case 33 The Rate-Determining Step in the S N Ar Reaction....Pages 217-223
Level 3 - Case 34 Helicenophanes and their Racemization....Pages 225-230
Level 3 - Case 35 Solvolysis of Vinyl Iodonium Salts....Pages 231-236
Level 3 - Case 36 Vicarious Nucleophilic Substitution....Pages 237-242
Level 3 - Case 37 Base-promoted HF Elimination from 4-Fluoro-4-(4’nitrophenyl)butan-2-one....Pages 243-250
Level 3 - Case 38 Substitution of β-Halostyrenes by MeS - ....Pages 251-258
Level 3 - Case 39 Periodinane-Mediated Cyclization of Anilides....Pages 259-268
Level 3 - Case 40 Solvolysis of 8-Deltacyclyl Brosylates....Pages 269-276
Back Matter....Pages 277-290