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Level 1
Case 1. A Surprise in the Synthesis of Guanacastepene A ..................................1
Case 2. Sulfenylation of Indole ........................................................7
Case 3. Substrate Selective Reactions in the Presence of Lewis Acids............. 13
Case 4. Diastereoselective Reductions of P-Ketoesters ....................................21
Case 5. Rearrangements from Tetrahydropyran Derivatives ............................27
Case 6. Stereospecific Substitution Reactions of Epoxy Sulfides ..................... 33
Case 7. NaBH4 Reduction of a,p-Unsaturated Chromium Carbene Complexes ............... 39
Case 8. Addition of Hydroxylamines to a,p-Unsaturated Esters ......................47
Case 9. Solvolysis of Electron-Deficient Norbornyl Triflates........................... 55
Case 10 Nucleophile Versus Base Catalysis ......................................................63
Case 11. The Hydrolysis ofp-Substituted Styrene Oxides.................................69
Case 12. Elimination Reactions of Benzaldehyde O-Benzoyloximes .................79
Case 13. Oxygen Versus Sulfur Stabilization of Carbenium Ions....................... 87
Case 14. Cyclization of 2,3-Dibenzylidenesuccinates.........................................97
Case 15. Oxazoline N-Oxides as Dipoles in [3+2] Cycloadditions ...................101
Case 16. Light-Induced Cycloadditions of N-Phthaloyl a-Amino Acids ..........107
Level 2
Case 17. Change in Rate-Determining Step in an ElcB Mechanism: Aminolysis of Sulfamate Esters............... 113
Case 18. Unusual Diels-Alder Reactivity of Acyclic 2-Azadienes ...................119
Case 19. Chelate-Controlled Carbonyl Addition Reactions ..............................125
Case 20. Esterification of Carboxylic Acids with Dimethyl Carbonate and DBU ...................... 131
Case 21. A Hammett Analysis in a Multistep Reaction:
Rhodium(II)-Catalyzed Decomposition of a-Diazo Esters ................139
Case 22. Tandem Cycloadditions with Nitronates ............................................145
Case 23. Hydrolysis of 2-Aminobenzoate Esters.................................. . 153
Case 24. Rearrangements of Cyclobutenones ..................................................159
Case 25. Epoxi Ester-Orthoester Rearrangement............................................. 163
Case 26. 2-Chloro-l,3,5-triazines as Activating Groups of Carboxylic
Acids in the Formation of Peptide Bonds........................................... 169
Case 27. Acid-Catalyzed Isomerization of Imines ............................................ 177
Case 28. A Dearomatizing Disrotatory Electrocyclic Ring Closure ................. 183
Case 29. Stereoselective Debromination of Vicinal Dibromides ...................... 189
Case 30. Diels-Alder Reactions of N-Acyl-1,2,4,5-tetrazines........................... 197
Case 31. Stereoselective Synthesis of 2-Acylaziridines ....................................203
Level 3
Case 32. The Baylis-Hillman Reaction .......................................................... 211
Case 33. The Rate-Determining Step in the SNAr Reaction.............................. 217
Case 34. Helicenophanes and their Racemization............................................ 225
Case 35. Solvolysis of Vinyl Iodonium Salts...................................................231
Case 36. Vicarious Nucleophilic Substitution...................................................237
Case 37. Base-promoted HF Elimination from
4-Fluoro-4-(4'-nitrophenyl)butan-2-one ...........................................243
Case 38. Substitution of P-Halostyrenes by MeS. ........................................... 251
Case 39. Periodinane-Mediated Cyclization of Anilides .................................. 259
Case 40. Solvolysis of 8-Deltacyclyl Brosylates............................................... 269
Library of Congress Subject Headings for this publication: Organic reaction mechanisms