Frontier Orbitals and Organic Chemical Reactions

Cover......Page 1
Contents......Page 3
1 Introduction......Page 4
2.1 Chemical Bonds......Page 8
2.2 Frontier Orbitals: HOMO and LUMO......Page 26
3 Ionic Reactions......Page 36
3.1 The Principle of Hard and Soft Acids and Bases......Page 37
3.2 Ambident Nucleophiles......Page 43
3.4 Substitution at a Saturated Carbon Atom......Page 77
3.5 The alpha-Effect......Page 80
3.6 Some Applications of Perturbation Theory......Page 82
4 Thermal Pericyclic Reactions......Page 89
4.1 The Woodward-Hoffmann Rules......Page 90
4.2 The Rates of Cycloaddition Reactions......Page 113
4.3 Estimating the Energies and Coefficients of the Frontier Orbitals......Page 117
4.4 Examples of Regioselectivity......Page 130
4.5 Lewis Acid Catalysis of Diels-Alder Reactions......Page 164
4.6 Site Selectivity in Cycloadditions......Page 168
4.7 Periselectivity in Pericyclic Reactions......Page 176
5.1 Introduction: Nucleophilic and Electrophilic Radicals......Page 185
5.2 The Abstraction of Hydrogen and Halogen Atoms......Page 189
5.3 The Addiction of Radicals to pi-Bonds......Page 191
5.4 Ambident Radicals......Page 198
5.5 Radical Coupling......Page 205
5.6 Photochemically-Induced Radical Reactions......Page 207
6.1 Photochemical Reactions in General......Page 211
6.2 The Photochemical Woodward-Hoffmann Rule......Page 213
6.3 Regioselectivity of Photocycloaddictions......Page 216
6.4 Photochemical Aromatic Substitution Reactions......Page 226
7 Exceptions......Page 231
References......Page 233
Index......Page 246
Back Cover......Page 253