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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 | |