1. Introduction.
Mechanisms of Reactions. Electron Delocalization and Resonance.
2. Electrocyclic Reactions.
Introduction. Conrotatory and Disrotatory Processes. Explanations
for the Woodward-Hoffman Rules. Electrocyclic Reactions with Odd
Numbers of Atoms. Photochemical Cyclizations.
3. Cycloaddiction and Cycloreversion Reactions.
Introduction. Suprafacial and Antarafacial Addition. Selection
Rules for Cycloaddition and Cycloreversion Reactions. Examples of
Thermal Cycloaddition Reactions. Photochemical Cycloadditions.
4. Sigmatropic Reactions.
Theory of Sigmatropic Shifts. Experimental Observations.
Sigmatropic Rearrangements of Charged Systems.
5. Linear Free-Energy Relationships.
The Hammett Equation. Separation of Polar, Resonance, and Steric
Effects.
6. Migrations to Electron-Deficient Centers.
Migrations to Electron-Deficient Carbons. The Nature of the
Migrating Groups. Rearrangements of Carbocations. Long-Distance
Migrations. Migrations to Nitrogen and Oxygen.
7. Neighboring-Group Effects and “Nonclassical” Cations.
Substitution with Retention of Configuration. Cyclic Halonium Ions.
Sulfur and Nitrogen Mustards. Trans/Cis Rate Ratios. Neighboring
Acetoxy Groups. Cyclic Phenonium Ions. Double Bonds as Neighboring
Groups. Cyclopropane Rings as Neighboring Groups. Neighboring Alkyl
Groups: 2-Norbornyl Cations.
8. Rearrangements of Carbanions and Free Radicals.
Carbanion Rearrangements. Rearrangements of Free Radicals.
9. Carbenes, Carbenoids, and Nitrenes.
Introduction. Formation of Carbenes and Nitrenes. Singlet and
Triplet Carbenes. Additions to Double Bonds. Insertion Reactions.
Rearrangements.
10. Six-Membered Heterocyclic Rings.
Aromatic Heterocyclic Molecules. Reactions of Pyridine and Its
Analogs. Synthesis of Six-Membered Heterocyclic Rings.
11. Five-Membered Heterocyclic Rings.
Introduction. Electron Delocalization and Aromaticity. Reactions of
Five-Membered Heterocyclic Rings. Synthesis of Five-Membered
Heteroaromatic Rings.
Index.
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