Elsevier S & T

Advanced Organic Chemistry: Reaction Mechanisms

Bruckner, Reinhard

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Table of contents
  • Contentsv
  • Chapter 1. Radical Substitution Reactions at the Saturated C Atom1
  • 1.1 Bonding and Preferred Geometries in C Radicals, Carbenium Ions and Carbanions1
  • 1.2 Stability of Radicals5
  • 1.3 Relative Rates of Analogous Radical Reactions9
  • 1.4 Radical Substitution Reactions: Chain Reactions13
  • 1.5 Radical Initiators15
  • 1.6 Radical Chemistry of Alkylmercury(II) Hydrides16
  • 1.7 Radical Halogenation of Hydrocarbons19
  • 1.8 Autoxidations32
  • 1.9 Defunctionalizations via Radical Substitution Reactions34
  • References40
  • Chapter 2. Nucleophilic Substitution Reactions at the Saturated C Atom43
  • 2.1 Nucleophiles and Electrophiles; Leaving Groups43
  • 2.2 Good and Poor Nucleophiles44
  • 2.3 Leaving Groups and the Quality of Leaving Groups46
  • 2.4 SN2 Reactions: Kinetic and Stereochemical Analysis„Substituent Effects on Reactivity49
  • 2.5 SN1 Reactions: Kinetic and Stereochemical Analysis; Substituent Effects on Reactivity57
  • 2.6 When Do SN Reactions at Saturated C Atoms Take Place According to the SN1 Mechanism and When Do69
  • 2.7 Unimolecular SN Reactions That Do Not Take Place via Simple Carbenium Ion Intermediates: Neighbo69
  • 2.8 Preparatively Useful SN2 Reactions: Alkylations76
  • References81
  • Chapter 3. Additions to the Olefinic C=C Double Bond85
  • 3.1 The Concept of cis and trans Addition86
  • 3.2 Vocabulary of Stereochemistry and Stereoselective Synthesis I87
  • 3.3 Additions That Take Place Diastereoselectivity as cis Additions91
  • 3.4 Enantioselective cis Additions to C=C Double Bonds105
  • 3.5 Additions That Take Place Diastereoselectively as trans Additions (Additions via Onium Intermedi116
  • 3.6 Additions That Take Place or Can Take Place without Stereocontrol Depending on the Mechanism123
  • References126
  • Chapter 4. β-Eliminations129
  • 4.1 Concepts of Elimination Reactions129
  • 4.2 b-Eliminations of H/Het via Cyclic Transition States136
  • 4.3 b-Eliminations of H/Het via Acyclic Transition States: The Mechanistic Alternatives140
  • 4.4 E2 Eliminations of H/Het and the E2/SN2 Competition141
  • 4.5 E1 Elimination of H/Het from Rtert„X and the E1/SN1 Competition149
  • 4.6 E1cb Eliminations156
  • 4.7 β-Eliminations of Het1/Het2160
  • References166
  • Chapter 5. Substitution Reactions on Aromatic Compounds169
  • 5.1 Electrophilic Aromatic Substitutions via Wheland Complexes ("Ar-SE Reactions")169
  • 5.2 Ar-SE Reactions via Wheland Complexes: Individual Reactions182
  • 5.3 Electrophilic Substitution Reactions on Metallated Aromatic Compounds200
  • 5.4 Nucleophilic Substitution Reactions in Aryldiazonium Salts207
  • 5.5 Nucleophilic Substitution Reactions via Meisenheimer Complexes211
  • 5.6 Nucleophilic Aromatic Substitution via Arynes, cine Substitution216
  • References217
  • Chapter 6. Nucleophilic Substitution Reactions on the Carboxyl Carbon (Except through Enolates)221
  • 6.1 C=O-Containing Substrates and Their Reactions with Nucleophiles221
  • 6.2 Mechanisms, Rate Laws, and Rate of Nucleophilic Substitution Reactions at the Carboxyl Carbon224
  • 6.3 Activation of Carboxylic Acids and of Carboxylic Acid Derivatives236
  • 6.4 Selected SN Reactions of Heteroatom Nucleophiles on the Carboxyl Carbon244
  • 6.5 SN Reactions of Hydride Donors, Organometallics, and Heteroatom-Stabilized "Carbanions" on the C260
  • References268
  • Chapter 7. Additions of Heteroatom Nucleophiles to Heterocumulenes. Additions of Heteroatom Nucleoph271
  • 7.1 Additions of Heteroatom Nucleophiles to Heterocumulenes271
  • 7.2 Additions of Heteroatom Nucleophiles to Carbonyl Compounds279
  • 7.3 Addition of Heteroatom Nucleophiles to Carbonyl Compounds in Combination with Subsequent SN1 Rea288
  • 7.4 Addition of Nitrogen Nucleophiles to Carbonyl Compounds in Combination with Subsequent E1 Elimin299
  • References303
  • Chapter 8. Addition of Hydride Donors and Organometallic Compounds to Carbonyl Compounds305
  • 8.1 Suitable Hydride Donors and Organometallic Compounds and a Survey of the Structure of Organometa305
  • 8.2 Chemoselectivity of the Addition of Hydride Donors to Carbonyl Compounds307
  • 8.3 Diastereoselectivity of the Addition of Hydride Donors to Carbonyl Compounds309
  • 8.4 Enantioselective Addition of Hydride Donors to Carbonyl Compounds323
  • 8.5 Addition of Organometallic Compounds to Carbonyl Compounds327
  • 8.6 1,4 -Additions of Organometallic Compounds to α,β-Unsaturated Ketones339
  • References342
  • Chapter 9. Reaction of Ylides with Saturated or α,β-Unsaturated Carbonyl Compounds347
  • 9.1 Ylides/Ylenes347
  • 9.2 Reactions of S Ylides with Saturated Carbonyl Compounds or with Michael Acceptors: Three-Membere349
  • 9.3 Condensation of P Ylides with Carbonyl Compounds: Wittig Reaction353
  • 9.4 Horner–Wadsworth–Emmons Reaction360
  • References372
  • Chapter 10. Chemistry of the Alkaline Earth Metal Enolates373
  • 10.1 Basic Considerations373
  • 10.2 Alkylation of Quantitatively Prepared Enolates and Aza-Enolates; Chain-Elongating Syntheses of391
  • 10.3 Hydroxyalkylation of Enolates with Carbonyl Compounds ("Aldol Addition"): Synthesis of β-Hydro406
  • 10.4 Condensation of Enolates with Carbonyl Compounds: Synthesis of Michael Acceptors414
  • 10.5 Acylation of Enolates422
  • 10.6 Michael Additions of Enolates428
  • References432
  • Chapter 11. Rearrangements435
  • 11.1 Nomenclature of Sigmatropic Shifts435
  • 11.2 Molecular Origins for the Occurrence of [1,2]-Rearrangements436
  • 11.3 [1,2]-Rearrangements in Species with a Valence Electron Sextet438
  • 11.4 [1,2]-Rearrangements without the Occurrence of a Sextet Intermediate458
  • 11.5 Claisen Rearrangement467
  • References474
  • Chapter 12. Thermal Cycloadditions477
  • 12.1 Driving Force and Feasibility of One-Step [2+4 ]- and [2+2]-Cycloadditions477
  • 12.2 Transition State Structures of Selected One-Step [2+4 ]- and [2+2]-Cycloadditions478
  • 12.3 Diels–Alder Reactions488
  • 12.4 [2+2]-Cycloadditions with Dichloroketene502
  • 12.5 1,3-Dipolar Cycloadditions504
  • References516
  • Chapter 13. Transition Metal-Mediated Alkenylations, Arylations, and Alkynylations519
  • 13.1 Alkenylation and Arylation of Copper-Bound Organyl Groups520
  • 13.2 Alkenylation and Arylation of Grignard Compounds522
  • 13.3 Palladium-Catalyzed Alkenylation and Arylation of Organometallic Compounds526
  • 13.4 Alkynylation of Copper Acetylides538
  • 13.5 Heck Reactions539
  • References542
  • Chapter 14. Oxidations and Reductions545
  • 14.1 Oxidation States of Organic Chemical Compounds, Oxidation Numbers in Organic Chemical Compounds545
  • 14.2 Cross-References to Redox Reactions Already Discussed in Chapters 1–13550
  • 14.3 Oxidations555
  • 14.4 Reductions576
  • References608
  • Index613
Book details
  • Vendor Elsevier S & T
  • SKU 9780121381103R90
  • ISBN-13 9780080498805
  • Author Bruckner, Reinhard
  • Category Science
  • Subject Organic

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A best-selling mechanistic organic chemistry text in Germany, this text's translation into English fills a long-existing need for a modern, thorough and accessible treatment of reaction mechanisms for students of organic chemistry at the advanced undergraduate and graduate level. Knowledge of reaction mechanisms is essential to all applied areas of organic chemistry; this text fulfills that need by presenting the right material at the right level.