Advanced Organic Chemistry Reaction Mechanisms

ISBN-10: 0121381102

ISBN-13: 9780121381103

Edition: 2002

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Knowledge of reaction mechanisms is essential to all applied areas of organic chemistry, and this text covers and explains fully the most recently developed reactions.
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Book details

List price: $139.00
Copyright year: 2002
Publisher: Elsevier Science & Technology Books
Publication date: 7/12/2001
Binding: Hardcover
Pages: 636
Size: 7.50" wide x 9.25" long x 1.25" tall
Weight: 2.838
Language: English

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