March's Advanced Organic Chemistry

1 - March's Advanced Organic Chemistry [Seite 3]
2 - Contents [Seite 7]
3 - New Reaction Sections Correlation: 7th edition ? 8th edition [Seite 17]
3.1 - 7th ? 8th [Seite 17]
4 - Preface [Seite 23]
5 - Common Abbreviations [Seite 27]
6 - Biographical Statement [Seite 33]
7 - New Features of the 8th Edition [Seite 35]
8 - PART I INTRODUCTION [Seite 37]
8.1 - 1 Localized Chemical Bonding [Seite 39]
8.1.1 - 1.A Covalent Bonding [Seite 39]
8.1.2 - 1.B Multiple Valence [Seite 43]
8.1.3 - 1.C Hybridization [Seite 43]
8.1.4 - 1.D Multiple Bonds [Seite 45]
8.1.5 - 1.E Photoelectron Spectroscopy [Seite 48]
8.1.6 - 1.F Electronic Structures of Molecules [Seite 51]
8.1.7 - 1.G Electronegativity [Seite 53]
8.1.8 - 1.H Dipole Moment [Seite 55]
8.1.9 - 1.I Inductive and Field Effects [Seite 56]
8.1.10 - 1.J Bond Distances [Seite 59]
8.1.11 - 1.K Bond Angles [Seite 63]
8.1.12 - 1.L Bond Energies [Seite 65]
8.2 - 2 Delocalized Chemical Bonding [Seite 69]
8.2.1 - 2.A Molecular Orbitals [Seite 70]
8.2.2 - 2.B Bond Energies and Distances in Compounds Containing Delocalized Bonds [Seite 73]
8.2.3 - 2.C Molecules that have Delocalized Bonds [Seite 75]
8.2.4 - 2.D Cross Conjugation [Seite 80]
8.2.5 - 2.E The Rules of Resonance [Seite 82]
8.2.6 - 2.F The Resonance Effect [Seite 84]
8.2.7 - 2.G Steric Inhibition of Resonance and the Influences of Strain [Seite 84]
8.2.8 - 2.H p??????-d?????? Bonding: Ylids [Seite 88]
8.2.9 - 2.I Aromaticity [Seite 90]
8.2.9.1 - 2.I.i Six-Membered Rings [Seite 94]
8.2.9.2 - 2.I.ii Five-, Seven-, and Eight-Membered Rings [Seite 98]
8.2.9.3 - 2.I.iii Other Systems Containing Aromatic Sextets [Seite 103]
8.2.10 - 2.J Alternant and Nonalternant Hydrocarbons [Seite 104]
8.2.11 - 2.K Aromatic Systems with Electron Numbers Other Than Six [Seite 106]
8.2.11.1 - 2.K.i Systems of Two Electrons [Seite 108]
8.2.11.2 - 2.K.ii Systems of Four Electrons: Antiaromaticity [Seite 109]
8.2.11.3 - 2.K.iii Systems of Eight Electrons [Seite 112]
8.2.11.4 - 2.K.iv Systems of Ten Electrons [Seite 113]
8.2.11.5 - 2.K.v Systems of More than Ten Electrons: 4n+2 Electrons [Seite 116]
8.2.11.6 - 2.K.vi Systems of More Than Ten Electrons: 4n Electrons [Seite 121]
8.2.12 - 2.L Other Aromatic Compounds [Seite 125]
8.2.13 - 2.M Hyperconjugation [Seite 128]
8.2.14 - 2.N Tautomerism [Seite 132]
8.2.14.1 - 2.N.i Keto-Enol Tautomerism [Seite 133]
8.2.14.2 - 2.N.ii Other Proton-Shift Tautomerism [Seite 136]
8.3 - 3 Bonding Weaker Than Covalent [Seite 141]
8.3.1 - 3.A Hydrogen Bonding [Seite 141]
8.3.2 - 3.B ??????-?????? Interactions [Seite 149]
8.3.3 - 3.C Addition Compounds [Seite 150]
8.3.3.1 - 3.C.i Electron Donor-Acceptor (EDA) Complexes [Seite 150]
8.3.3.2 - 3.C.ii Crown Ether Complexes and Cryptates [Seite 153]
8.3.3.3 - 3.C.iii Inclusion Compounds [Seite 158]
8.3.3.4 - 3.C.iv Cyclodextrins [Seite 161]
8.3.4 - 3.D Catenanes and Rotaxanes [Seite 163]
8.3.5 - 3.E Cucurbit[n]Uril-Based Gyroscane [Seite 167]
8.4 - 4 Stereochemistry and Conformation [Seite 169]
8.4.1 - 4.A Optical Activity and Chirality [Seite 169]
8.4.2 - 4.B Dependence of Rotation on Conditions of Measurement [Seite 171]
8.4.3 - 4.C What Kinds of Molecules Display Optical Activity? [Seite 172]
8.4.4 - 4.D The Fischer Projection [Seite 183]
8.4.5 - 4.E Absolute Configuration [Seite 184]
8.4.5.1 - 4.E.i The Cahn-Ingold-Prelog System [Seite 186]
8.4.5.2 - 4.E.ii Methods Of Determining Configuration [Seite 188]
8.4.6 - 4.F The Cause of Optical Activity [Seite 192]
8.4.7 - 4.G Molecules with more than One Stereogenic Center [Seite 193]
8.4.8 - 4.H Asymmetric Synthesis [Seite 197]
8.4.9 - 4.I Methods of Resolution [Seite 202]
8.4.10 - 4.J Optical Purity [Seite 209]
8.4.11 - 4.K Cis-Trans Isomerism [Seite 211]
8.4.11.1 - 4.K.i Cis-Trans Isomerism Resulting from Double Bonds [Seite 211]
8.4.11.2 - 4.K.ii Cis-Trans Isomerism of Monocyclic Compounds [Seite 215]
8.4.11.3 - 4.K.iii Cis-Trans Isomerism of Fused and Bridged Ring Systems [Seite 216]
8.4.12 - 4.L Out-In Isomerism [Seite 217]
8.4.13 - 4.M Enantiotopic and Diastereotopic Atoms, Groups, and Faces [Seite 219]
8.4.14 - 4.N Stereospecific and Stereoselective Syntheses [Seite 222]
8.4.15 - 4.O Conformational Analysis [Seite 223]
8.4.15.1 - 4.O.i Conformation in Open-Chain Systems [Seite 224]
8.4.15.2 - 4.O.ii Conformation in Six-Membered Rings [Seite 230]
8.4.15.3 - 4.O.iii Conformation in Six-Membered Rings Containing Heteroatoms [Seite 235]
8.4.15.4 - 4.O.iv Conformation in Other Rings [Seite 238]
8.4.16 - 4.P Molecular Mechanics [Seite 240]
8.4.17 - 4.Q Strain [Seite 242]
8.4.17.1 - 4.Q.i Strain in Small Rings [Seite 243]
8.4.17.2 - 4.Q.ii Strain in Other Rings [Seite 249]
8.4.17.3 - 4.Q.iii Unsaturated Rings [Seite 251]
8.4.17.4 - 4.Q.iv Strain Due to Unavoidable Crowding [Seite 254]
8.5 - 5 Carbocations, Carbanions, Free Radicals, Carbenes, and Nitrenes [Seite 259]
8.5.1 - 5.A Carbocations [Seite 260]
8.5.1.1 - 5.A.i Nomenclature [Seite 260]
8.5.1.2 - 5.A.ii Stability and Structure of Carbocations [Seite 260]
8.5.1.3 - 5.A.iii The Generation And Fate Of Carbocations [Seite 270]
8.5.2 - 5.B Carbanions [Seite 273]
8.5.2.1 - 5.B.i Stability and Structure [Seite 273]
8.5.2.2 - 5.B.ii The Structure Of Organometallic Compounds [Seite 280]
8.5.2.3 - 5.B.iii The Generation And Fate Of Carbanions [Seite 285]
8.5.3 - 5.C Free Radicals [Seite 286]
8.5.3.1 - 5.C.i Stability and Structure [Seite 286]
8.5.3.2 - 5.C.ii The Generation and Fate of Free Radicals [Seite 297]
8.5.3.3 - 5.C.iii Radical Ions [Seite 301]
8.5.4 - 5.D Carbenes [Seite 302]
8.5.4.1 - 5.D.i Stability and Structure [Seite 302]
8.5.4.2 - 5.D.ii The Generation and Fate of Carbenes [Seite 305]
8.5.4.3 - 5.D.iii N-Heterocyclic Carbenes (NHCs) [Seite 310]
8.5.5 - 5.E Nitrenes [Seite 312]
8.6 - 6 Mechanisms and Methods of Determining Them [Seite 315]
8.6.1 - 6.A Types of Mechanism [Seite 315]
8.6.2 - 6.B Types of Reaction [Seite 316]
8.6.3 - 6.C Thermodynamic Requirements for Reaction [Seite 319]
8.6.4 - 6.D Kinetic Requirements for Reaction [Seite 320]
8.6.5 - 6.E The Baldwin Rules for Ring Closure [Seite 324]
8.6.6 - 6.F Kinetic and Thermodynamic Control [Seite 326]
8.6.7 - 6.G The Hammond Postulate [Seite 327]
8.6.8 - 6.H Microscopic Reversibility [Seite 327]
8.6.9 - 6.I Marcus Theory [Seite 328]
8.6.10 - 6.J Methods of Determining Mechanisms [Seite 329]
8.6.10.1 - 6.J.i Identification of Products [Seite 329]
8.6.10.2 - 6.J.ii Determination of the Presence of an Intermediate [Seite 330]
8.6.10.3 - 6.J.iii The Study of Catalysis [Seite 331]
8.6.10.4 - 6.J.iv Isotopic Labeling [Seite 332]
8.6.10.5 - 6.J.v Stereochemical Evidence [Seite 332]
8.6.10.6 - 6.J.vi Kinetic Evidence [Seite 333]
8.6.10.7 - 6.J.vii Isotope Effects [Seite 340]
8.6.11 - 6.K Catalyst Development [Seite 344]
8.7 - 7 Irradiation Processes and Techniques that Influence Reactions in Organic Chemistry [Seite 349]
8.7.1 - 7.A Photochemistry [Seite 350]
8.7.1.1 - 7.A.i Excited States and the Ground State [Seite 350]
8.7.1.2 - 7.A.ii Singlet and Triplet States: "Forbidden" Transitions [Seite 352]
8.7.1.3 - 7.A.iii Types of Excitation [Seite 353]
8.7.1.4 - 7.A.iv Nomenclature and Properties of Excited States [Seite 354]
8.7.1.5 - 7.A.v Photolytic Cleavage [Seite 355]
8.7.1.6 - 7.A.vi The Fate of the Excited Molecule: Physical Processes [Seite 356]
8.7.1.7 - 7.A.vii The Fate of the Excited Molecule: Chemical Processes [Seite 361]
8.7.1.8 - 7.A.viii The Determination of Photochemical MechanismsFor a review, see Calvert, J.G. [Seite 366]
8.7.2 - 7.B Sonochemistry [Seite 367]
8.7.3 - 7.C Microwave Chemistry [Seite 370]
8.7.4 - 7.D Flow Chemistry [Seite 372]
8.7.5 - 7.E Mechanochemistry [Seite 374]
8.8 - 8 Acids and Bases [Seite 375]
8.8.1 - 8.A Brønsted Theory [Seite 375]
8.8.1.1 - 8.A.i Brønsted Acids [Seite 376]
8.8.1.2 - 8.A.ii Brønsted Bases [Seite 383]
8.8.2 - 8.B The Mechanism of Proton Transfer Reactions [Seite 386]
8.8.3 - 8.C Measurements of Solvent Acidity [Seite 388]
8.8.4 - 8.D Acid and Base Catalysis [Seite 391]
8.8.5 - 8.E Lewis Acids and Bases [Seite 393]
8.8.5.1 - 8.E.i Hard-Soft Acids-Bases [Seite 395]
8.8.6 - 8.F The Effects of Structure on the Strengths of Acids and Bases [Seite 397]
8.8.7 - 8.G The Effects of the Medium on Acid and Base Strength [Seite 406]
8.9 - 9 Effects of Structure and Medium on Reactivity [Seite 411]
8.9.1 - 9.A Resonance and Field Effects [Seite 411]
8.9.2 - 9.B Steric Effects [Seite 413]
8.9.3 - 9.C Quantitative Treatments of the Effect of Structure on Reactivity [Seite 416]
8.9.4 - 9.D Effect of Medium on Reactivity and Rate [Seite 426]
8.9.5 - 9.E High Pressure [Seite 426]
8.9.6 - 9.F Water and Other Nonorganic Solvents [Seite 427]
8.9.7 - 9.G Ionic Liquid Solvents [Seite 429]
8.9.8 - 9.H Solventless Reactions [Seite 431]
9 - PART II INTRODUCTION [Seite 433]
9.1 - II.A IUPAC Nomenclature for Transformations [Seite 434]
9.2 - II.B IUPAC System for Symbolic Representation of Mechanisms [Seite 434]
9.2.1 - Step 1, First Symbol [Seite 435]
9.2.2 - Step 1, Second Symbol [Seite 435]
9.2.3 - Step 1, Combined Symbols [Seite 435]
9.2.4 - Step 2 [Seite 436]
9.2.5 - Overall [Seite 436]
9.3 - II.C Organic Syntheses References [Seite 436]
9.4 - 10 Aliphatic Substitution, Nucleophilic and Organometallic [Seite 439]
9.4.1 - 10.A Mechanisms [Seite 440]
9.4.1.1 - 10.A.i The SN2 Mechanism [Seite 440]
9.4.1.2 - 10.A.ii The SN1 Mechanism [Seite 446]
9.4.1.3 - 10.A.iii Ion Pairs in the SN1 Mechanism [Seite 450]
9.4.1.4 - 10.A.iv Mixed SN1 and SN2 Mechanisms [Seite 454]
9.4.2 - 10.B SET Mechanisms [Seite 456]
9.4.3 - 10.C The Neighboring-Group Mechanism [Seite 458]
9.4.3.1 - 10.C.i Neighboring-Group Participation by ?????? and ?????? Bonds: Nonclassical Carbocations [Seite 461]
9.4.4 - 10.D The SNi Mechanism [Seite 476]
9.4.5 - 10.E Nucleophilic Substitution at an Allylic Carbon: Allylic Rearrangements [Seite 477]
9.4.6 - 10.F Nucleophilic Substitution at an Aliphatic Trigonal Carbon: The Tetrahedral Mechanism [Seite 481]
9.4.7 - 10.G Reactivity [Seite 485]
9.4.7.1 - 10.G.i The Effect of Substrate Structure [Seite 485]
9.4.7.2 - 10.G.ii The Effect of the Attacking Nucleophile [Seite 493]
9.4.7.3 - 10.G.iii The Effect of the Leaving Group [Seite 500]
9.4.7.4 - 10.G.iv The Effect of the Reaction Medium [Seite 505]
9.4.7.5 - 10.G.v Phase-Transfer Catalysis [Seite 510]
9.4.7.6 - 10.G.vi Influencing Reactivity by External Means [Seite 513]
9.4.7.7 - 10.G.vii Ambident (Bidentant) Nucleophiles: Regioselectivity [Seite 514]
9.4.7.8 - 10.G.viii Ambident Substrates [Seite 517]
9.4.8 - 10.H Reactions [Seite 519]
9.4.8.1 - 10.H.i Oxygen Nucleophiles [Seite 519]
9.4.8.2 - 10.H.ii Sulfur Nucleophiles [Seite 542]
9.4.8.3 - 10.H.iii Nitrogen Nucleophiles [Seite 548]
9.4.8.4 - 10.H.iv Halogen Nucleophiles [Seite 570]
9.4.8.5 - 10.H.v Carbon Nucleophiles [Seite 581]
9.5 - 11 Aromatic Substitution, Electrophilic [Seite 643]
9.5.1 - 11.A Mechanisms [Seite 643]
9.5.1.1 - 11.A.i The Arenium Ion Mechanism [Seite 644]
9.5.1.2 - 11.A.ii The SE1 Mechanism [Seite 649]
9.5.2 - 11.B Orientation and Reactivity [Seite 650]
9.5.2.1 - 11.B.i Orientation and Reactivity in Monosubstituted Benzene Rings [Seite 650]
9.5.2.2 - 11.B.ii The Ortho/Para Ratio [Seite 654]
9.5.2.3 - 11.B.iii Ipso Attack [Seite 656]
9.5.2.4 - 11.B.iv Orientation in Benzene Rings With More Than One Substituent [Seite 657]
9.5.2.5 - 11.B.v Orientation in Other Ring Systems [Seite 658]
9.5.3 - 11.C Quantitative Treatments of Reactivity in the Substrate [Seite 660]
9.5.4 - 11.D A Quantitative Treatment of Reactivity of the Electrophile [Seite 662]
9.5.5 - 11.E The Effect of the Leaving Group [Seite 664]
9.5.6 - 11.F Reactions [Seite 665]
9.5.6.1 - 11.F.i Hydrogen as the Leaving Group in Simple Substitution Reactions [Seite 665]
9.5.6.2 - 11.F.ii Hydrogen As The Leaving Group In Rearrangement Reactions [Seite 711]
9.5.6.3 - 11.F.iii Other Leaving Groups [Seite 716]
9.6 - 12 Aliphatic, Alkenyl, and Alkynyl Substitution: Electrophilic and Organometallic [Seite 723]
9.6.1 - 12.A Mechanisms [Seite 723]
9.6.1.1 - 12.A.i Bimolecular Mechanisms. SE2 and SEi [Seite 724]
9.6.1.2 - 12.A.ii The SE1 Mechanism [Seite 727]
9.6.1.3 - 12.A.iii Electrophilic Substitution Accompanied by Double-Bond Shifts [Seite 730]
9.6.1.4 - 12.A.iv Other Mechanisms [Seite 731]
9.6.2 - 12.B Reactivity [Seite 731]
9.6.3 - 12.C Reactions [Seite 733]
9.6.3.1 - 12.C.i Hydrogen as Leaving Group [Seite 733]
9.6.3.2 - 12.C.ii Metals as Leaving Groups [Seite 769]
9.6.3.3 - 12.C.iii Halogen as Leaving Group [Seite 782]
9.6.3.4 - 12.C.iv Carbon Leaving Groups [Seite 787]
9.6.3.5 - 12.C.v Electrophilic Substitution At Nitrogen [Seite 796]
9.7 - 13 Aromatic Substitution: Nucleophilic and Organometallic [Seite 803]
9.7.1 - 13.A Mechanisms [Seite 804]
9.7.1.1 - 13.A.i The SNAr Mechanism [Seite 804]
9.7.1.2 - 13.A.ii The SN1 Mechanism [Seite 807]
9.7.1.3 - 13.A.iii The Benzyne Mechanism [Seite 808]
9.7.1.4 - 13.A.iv The SRN1 Mechanism [Seite 810]
9.7.1.5 - 13.A.v Other Mechanisms [Seite 812]
9.7.2 - 13.B Reactivity [Seite 812]
9.7.2.1 - 13.B.i The Effect of Substrate Structure [Seite 812]
9.7.2.2 - 13.B.ii The Effect of the Leaving Group [Seite 814]
9.7.2.3 - 13.B.iii The Effect of the Attacking Nucleophile [Seite 815]
9.7.3 - 13.C Reactions [Seite 815]
9.7.3.1 - 13.C.i All Leaving Groups Except Hydrogen And N2+ [Seite 815]
9.7.3.2 - 13.C.ii Hydrogen as Leaving Group [Seite 859]
9.7.3.3 - 13.C.iii Nitrogen as Leaving Group [Seite 860]
9.7.3.4 - 13.C.iv Rearrangements [Seite 870]
9.8 - 14 Radical Reactions [Seite 875]
9.8.1 - 14.A Mechanisms [Seite 875]
9.8.1.1 - 14.A.i Radical Mechanisms in General [Seite 875]
9.8.1.2 - 14.A.ii Free-Radical Substitution Mechanisms [Seite 880]
9.8.1.3 - 14.A.iii Mechanisms at an Aromatic Substrate [Seite 881]
9.8.1.4 - 14.A.iv Neighboring-Group Assistance in Free-Radical Reactions [Seite 883]
9.8.2 - 14.B Reactivity [Seite 884]
9.8.2.1 - 14.B.i Reactivity for Aliphatic Substrates [Seite 884]
9.8.2.2 - 14.B.ii Reactivity at a Bridgehead [Seite 889]
9.8.2.3 - 14.B.iii Reactivity in Aromatic Substrates [Seite 890]
9.8.2.4 - 14.B.iv Reactivity in the Attacking Radical [Seite 891]
9.8.2.5 - 14.B.v The Effect of Solvent on Reactivity [Seite 892]
9.8.3 - 14.C Reactions [Seite 892]
9.8.3.1 - 14.C.i Hydrogen as Leaving Group [Seite 892]
9.8.3.2 - 14.C.ii Metals as Leaving Groups [Seite 916]
9.8.3.3 - 14.C.iii Halogen as Leaving Group [Seite 919]
9.8.3.4 - 14.C.iv Sulfur as Leaving Group [Seite 919]
9.8.3.5 - 14.C.v Carbon as Leaving Group [Seite 921]
9.9 - 15 Addition to Carbon-Carbon Multiple Bonds [Seite 927]
9.9.1 - 15.A Mechanisms [Seite 928]
9.9.1.1 - 15.A.i Electrophilic Addition [Seite 928]
9.9.1.2 - 15.A.ii Nucleophilic Addition [Seite 931]
9.9.1.3 - 15.A.iii Free-Radical Addition [Seite 932]
9.9.1.4 - 15.A.iv Cyclic Mechanisms [Seite 934]
9.9.1.5 - 15.A.v Addition to Conjugated Systems [Seite 934]
9.9.2 - 15.B Orientation and Reactivity [Seite 935]
9.9.2.1 - 15.B.i Reactivity [Seite 935]
9.9.2.2 - 15.B.ii Orientation [Seite 938]
9.9.2.3 - 15.B.iii Stereochemical Orientation [Seite 940]
9.9.2.4 - 15.B.iv Addition to Cyclopropane Rings [Seite 942]
9.9.3 - 15.C Reactions [Seite 944]
9.9.3.1 - 15.C.i Isomerization of Double and Triple Bonds [Seite 944]
9.9.3.2 - 15.C.ii Reactions in Which Hydrogen Adds to One Side [Seite 946]
9.9.3.3 - 15.C.iii Reactions in Which Hydrogen Adds to Neither Side [Seite 1028]
9.9.3.4 - 15.C.iv Cycloaddition Reactions [Seite 1063]
9.10 - 16 Addition to Carbon-Heteroatom Multiple Bonds [Seite 1123]
9.10.1 - 16.A Mechanism and Reactivity [Seite 1123]
9.10.1.1 - 16.A.i Nucleophilic Substitution at an Aliphatic Trigonal Carbon: The Tetrahedral Mechanism [Seite 1125]
9.10.2 - 16.B Reactions [Seite 1130]
9.10.2.1 - 16.B.i Reactions in Which Hydrogen or a Metallic Ion Adds to the Heteroatom [Seite 1131]
9.10.2.2 - 16.B.ii Acyl Substitution Reactions [Seite 1254]
9.10.2.3 - 16.B.iii Reactions in Which Carbon Adds to the Heteroatom [Seite 1293]
9.10.2.4 - 16.B.iv Addition to Isocyanides [Seite 1300]
9.10.2.5 - 16.B.v Nucleophilic Substitution at a Sulfonyl Sulfur Atom [Seite 1302]
9.11 - 17 Elimination Reactions [Seite 1309]
9.11.1 - 17.A Mechanisms and Orientation [Seite 1309]
9.11.1.1 - 17.A.i The E2 Mechanism [Seite 1310]
9.11.1.2 - 17.A.ii The E1 Mechanism [Seite 1316]
9.11.1.3 - 17.A.iii The E1cB Mechanism [Seite 1317]
9.11.1.4 - 17.A.iv The E1-E2-E1cB Spectrum [Seite 1322]
9.11.1.5 - 17.A.v The E2C Mechanism [Seite 1323]
9.11.2 - 17.B Regiochemistry of the Double Bond [Seite 1324]
9.11.3 - 17.C Stereochemistry of the Double Bond [Seite 1326]
9.11.4 - 17.D Reactivity [Seite 1327]
9.11.4.1 - 17.D.i Effect of Substrate Structure [Seite 1327]
9.11.4.2 - 17.D.ii Effect of the Attacking Base [Seite 1329]
9.11.4.3 - 17.D.iii Effect of the Leaving Group [Seite 1330]
9.11.4.4 - 17.D.iv Effect of the Medium [Seite 1330]
9.11.5 - 17.E Mechanisms and Orientation in Pyrolytic Eliminations [Seite 1331]
9.11.5.1 - 17.E.i Mechanisms [Seite 1331]
9.11.5.2 - 17.E.ii Orientation in Pyrolytic Eliminations [Seite 1334]
9.11.5.3 - 17.E.iii 1,4 Conjugate Eliminations [Seite 1334]
9.11.6 - 17.F Reactions [Seite 1335]
9.11.6.1 - 17.F.i Reactions in Which C=C and C?C Bonds Are Formed [Seite 1335]
9.11.6.2 - 17.F.ii Fragmentations [Seite 1357]
9.11.6.3 - 17.F.iii Reactions in Which C?N or C=N Bonds Are Formed [Seite 1361]
9.11.6.4 - 17.F.iv Reactions in Which C=O Bonds Are Formed [Seite 1364]
9.11.6.5 - 17.F.v Reactions in Which N=N Bonds Are Formed [Seite 1365]
9.11.6.6 - 17.F.vi Extrusion Reactions [Seite 1365]
9.12 - 18 Rearrangements [Seite 1371]
9.12.1 - 18.A Mechanisms [Seite 1372]
9.12.1.1 - 18.A.i Nucleophilic Rearrangements [Seite 1372]
9.12.1.2 - 18.A.ii The Actual Nature of the Migration [Seite 1373]
9.12.1.3 - 18.A.iii Migratory Aptitudes [Seite 1376]
9.12.1.4 - 18.A.iv Memory Effects [Seite 1379]
9.12.2 - 18.B Longer Nucleophilic Rearrangements [Seite 1380]
9.12.3 - 18.C Free-Radical Rearrangements [Seite 1381]
9.12.4 - 18.D Carbene Rearrangements [Seite 1385]
9.12.5 - 18.E Electrophilic Rearrangements [Seite 1385]
9.12.6 - 18.F Reactions [Seite 1386]
9.12.6.1 - 18.F.i 1,2-Rearrangements [Seite 1386]
9.12.6.2 - 18.F.ii Non 1,2-Rearrangements [Seite 1425]
9.13 - 19 Oxidations and Reductions [Seite 1475]
9.13.1 - 19.A Mechanisms [Seite 1476]
9.13.2 - 19.B Reactions [Seite 1478]
9.13.2.1 - 19.B.i Oxidations [Seite 1478]
9.13.2.2 - 19.B.ii Reductions [Seite 1546]
10 - Appendix A The Literature of Organic Chemistry [Seite 1643]
10.1 - A Primary Sources [Seite 1644]
10.1.1 - A.i Journals [Seite 1644]
10.1.2 - A.ii Patents [Seite 1645]
10.2 - B Secondary Sources [Seite 1649]
10.2.1 - B.i Listings of Titles [Seite 1649]
10.2.2 - B.ii Abstracts [Seite 1650]
10.2.3 - B.iii Beilstein [Seite 1653]
10.2.4 - B.iv Tables of Information [Seite 1655]
10.3 - C Reviews [Seite 1658]
10.3.1 - C.i Annual Reviews [Seite 1659]
10.3.2 - C.ii Awareness Services [Seite 1660]
10.3.3 - C.iii General Treatises [Seite 1661]
10.3.4 - C.iv Monographs and Treatises on Specific Areas [Seite 1663]
10.3.5 - C.v Textbooks [Seite 1663]
10.3.6 - C.vi Other Books [Seite 1664]
10.4 - D Literature Searching [Seite 1666]
10.4.1 - D.i Literature Searching Using Printed Materials [Seite 1666]
10.4.2 - D.ii Literature Searching Online [Seite 1668]
10.4.3 - D.iii Sci-Finder - the CAS database [Seite 1669]
10.4.4 - D.iv Science Citation Index [Seite 1671]
10.4.5 - D.v How to Locate Journal Articles [Seite 1675]
10.4.6 - D.vi Reaxys® [Seite 1676]
11 - Appendix B Classification of Reactions by Type of Compounds Synthesized [Seite 1681]
12 - Author Index [Seite 1705]
13 - Subject Index [Seite 1953]
14 - EULA [Seite 2141]