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| Foreword | |
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| Preface to the English Edition | |
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| Preface to the German Edition | |
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| Acknowledgments | |
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| Radical Substitution Reactions at the Saturated C Atom | |
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| Bonding and Preferred Geometries in C Radicals, Carbenium Ions and Carbanions | |
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| Stability of Radicals | |
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| Relative Rates of Analogous Radical Reactions | |
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| Radical Substitution Reactions: Chain Reactions | |
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| Radical Initiators | |
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| Radical Chemistry of Alkylmercury(II) Hydrides | |
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| Radical Halogenation of Hydrocarbons | |
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| Autoxidations | |
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| Defunctionalizations via Radical Substitution Reactions | |
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| References | |
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| Nucleophilic Substitution Reactions at the Saturated C Atom | |
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| Nucleophiles and Electrophiles; Leaving Groups | |
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| Good and Poor Nucleophiles | |
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| Leaving Groups and the Quality of Leaving Groups | |
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| S[subscript N]2 Reactions: Kinetic and Stereochemical Analysis--Substituent Effects on Reactivity | |
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| S[subscript N]1 Reactions: Kinetic and Stereochemical Analysis; Substituent Effects on Reactivity | |
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| When Do S[subscript N] Reactions at Saturated C Atoms Take Place According to the S[subscript N]1 Mechanism and When Do They Take Place According to the S[subscript N]2 Mechanism? | |
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| Unimolecular S[subscript N] Reactions That Do Not Take Place via Simple Carbenium Ion Intermediates: Neighboring Group Participation | |
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| Preparatively Useful S[subscript N]2 Reactions: Alkylations | |
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| References | |
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| Additions to the Olefinic C=C Double Bond | |
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| The Concept of cis and trans Addition | |
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| Vocabulary of Stereochemistry and Stereoselective Synthesis I | |
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| Additions That Take Place Diastereoselectivity as cis Additions | |
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| Enantioselective cis Additions to C=C Double Bonds | |
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| Additions That Take Place Diastereoselectively as trans Additions (Additions via Onium Intermediates) | |
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| Additions That Take Place or Can Take Place without Stereocontrol Depending on the Mechanism | |
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| References | |
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| [beta]-Eliminations | |
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| Concepts of Elimination Reactions | |
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| [beta]-Eliminations of H/Het via Cyclic Transition States | |
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| [beta]-Eliminations of H/Het via Acyclic Transition States: The Mechanistic Alternatives | |
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| E2 Eliminations of H/Het and the E2/S[subscript N]2 Competition | |
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| E1 Elimination of H/Het from R[subscript tert]--X and the E1/S[subscript N]1 Competition | |
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| E1[subscript cb] Eliminations | |
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| [beta]-Eliminations of Het[superscript 1]/Het[superscript 2] | |
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| References | |
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| Substitution Reactions on Aromatic Compounds | |
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| Electrophilic Aromatic Substitutions via Wheland Complexes ("Ar-S[subscript E] Reactions") | |
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| Ar-S[subscript E] Reactions via Wheland Complexes: Individual Reactions | |
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| Electrophilic Substitution Reactions on Metallated Aromatic Compounds | |
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| Nucleophilic Substitution Reactions in Aryldiazonium Salts | |
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| Nucleophilic Substitution Reactions via Meisenheimer Complexes | |
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| Nucleophilic Aromatic Substitution via Arynes, cine Substitution | |
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| References | |
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| Nucleophilic Substitution Reactions on the Carboxyl Carbon (Except through Enolates) | |
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| C=O-Containing Substrates and Their Reactions with Nucleophiles | |
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| Mechanisms, Rate Laws, and Rate of Nucleophilic Substitution Reactions at the Carboxyl Carbon | |
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| Activation of Carboxylic Acids and of Carboxylic Acid Derivatives | |
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| Selected S[subscript N] Reactions of Heteroatom Nucleophiles on the Carboxyl Carbon | |
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| S[subscript N] Reactions of Hydride Donors, Organometallics, and Heteroatom-Stabilized "Carbanions" on the Carboxyl Carbon | |
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| References | |
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| Additions of Heteroatom Nucleophiles to Heterocumulenes. Additions of Heteroatom Nucleophiles to Carbonyl Compounds and Follow-up Reactions | |
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| Additions of Heteroatom Nucleophiles to Heterocumulenes | |
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| Additions of Heteroatom Nucleophiles to Carbonyl Compounds | |
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| Addition of Heteroatom Nucleophiles to Carbonyl Compounds in Combination with Subsequent S[subscript N]1 Reactions: Acetalizations | |
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| Addition of Nitrogen Nucleophiles to Carbonyl Compounds in Combination with Subsequent E1 Eliminations: Condensation Reactions of Nitrogen Nucleophiles with Carbonyl Compounds | |
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| References | |
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| Addition of Hydride Donors and Organometallic Compounds to Carbonyl Compounds | |
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| Suitable Hydride Donors and Organometallic Compounds and a Survey of the Structure of Organometallic Compounds | |
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| Chemoselectivity of the Addition of Hydride Donors to Carbonyl Compounds | |
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| Diastereoselectivity of the Addition of Hydride Donors to Carbonyl Compounds | |
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| Enantioselective Addition of Hydride Donors to Carbonyl Compounds | |
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| Addition of Organometallic Compounds to Carbonyl Compounds | |
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| 1,4-Additions of Organometallic Compounds to [alpha],[beta]-Unsaturated Ketones | |
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| References | |
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| Reaction of Ylides with Saturated or [alpha],[beta]-Unsaturated Carbonyl Compounds | |
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| Ylides/Ylenes | |
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| Reactions of S Ylides with Saturated Carbonyl Compounds or with Michael Acceptors: Three-Membered Ring Formation | |
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| Condensation of P Ylides with Carbonyl Compounds: Wittig Reaction | |
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| Horner-Wadsworth-Emmons Reaction | |
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| References | |
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| Chemistry of the Alkaline Earth Metal Enolates | |
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| Basic Considerations | |
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| Alkylation of Quantitatively Prepared Enolates and Aza-Enolates; Chain-Elongating Syntheses of Carbonyl Compounds and Carboxylic Acid Derivatives | |
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| Hydroxyalkylation of Enolates with Carbonyl Compounds ("Aldol Addition"): Synthesis of [beta]-Hydroxyketones and [beta]-Hydroxyesters | |
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| Condensation of Enolates with Carbonyl Compounds: Synthesis of Michael Acceptors | |
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| Acylation of Enolates | |
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| Michael Additions of Enolates | |
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| References | |
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| Rearrangements | |
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| Nomenclature of Sigmatropic Shifts | |
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| Molecular Origins for the Occurrence of [1,2]-Rearrangements | |
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| [1,2]-Rearrangements in Species with a Valence Electron Sextet | |
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| [1,2]-Rearrangements without the Occurrence of a Sextet Intermediate | |
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| Claisen Rearrangement | |
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| References | |
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| Thermal Cycloadditions | |
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| Driving Force and Feasibility of One-Step [2 + 4]- and [2 + 2]-Cycloadditions | |
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| Transition State Structures of Selected One-Step [2 + 4]- and [2 + 2]-Cycloadditions | |
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| Diels-Alder Reactions | |
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| [2 + 2]-Cycloadditions with Dichloroketene | |
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| 1,3-Dipolar Cycloadditions | |
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| References | |
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| Transition Metal-Mediated Alkenylations, Arylations, and Alkynylations | |
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| Alkenylation and Arylation of Copper-Bound Organyl Groups | |
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| Alkenylation and Arylation of Grignard Compounds | |
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| Palladium-Catalyzed Alkenylation and Arylation of Organometallic Compounds | |
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| Alkynylation of Copper Acetylides | |
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| Heck Reactions | |
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| References | |
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| Oxidations and Reductions | |
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| Oxidation States of Organic Chemical Compounds, Oxidation Numbers in Organic Chemical Compounds, and Organic Chemical Redox Reactions | |
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| Cross-References to Redox Reactions Already Discussed in Chapters 1-13 | |
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| Oxidations | |
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| Reductions | |
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| References | |
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| Index | |