Organic Reactions Mechanisms

Автор(ы):Knipe A. C., Watts W. E.
06.10.2007
Год изд.:1997
Описание: The present volume, the thirty-third in the series, surveys research on organic reaction mechanisms described in the literature dated December 1996 to November 1997. In order to limit the size of the volume, the authors must necessarily exclude or restrict overlap with other publications which review specialist areas (e.g. photochemical reactions, biosynthesis, electrochemistry, organometallic chemistry, surface chemistry, and heterogeneous catalysis). In order to minimize duplication, while ensuring a comprehensive coverage, the Editors conduct a survey of all relevant literature and allocate publications to appropriate chapters. While a particular reference may be allocated to more than one chapter, the authors do assume that readers will be aware of the alternative chapters to which a borderline topic of interest may have been preferentially assigned.
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Organic Reactions Mechanisms — обложка книги.
CHAPTER 1 Reactions of Aldehydes and Ketones and their Derivatives B. A. MURRAY
Department of Applied Sciences, Institute of Technology Tallaght, Dublin, Ireland
  Formation and Reactions of Acetals and Related Species [1]
  Reactions of Glucosides and Nucleosides [4]
  Reactions of Ketenes [5]
  Formation and Reactions of Nitrogen Derivatives [6]
    Imines [6]
    Iminium ions and Related Species [8]
    Oximes, Hydrazones, and Related Species [9]
  С—С Bond Formation and Fission: Aldol and Related Reactions [10]
    Regio, Enantio-, and Diastereo-selective Aldol Reactions [10]
    Miscellaneous Aldol-type Reactions [12]
    Allylation Reactions [15]
  Other Addition Reactions [17]
    General and Theoretical [17]
    Protonation [18]
    Hydration and Hydrate Anions [19]
    Addition of Organometallics [20]
    Addition of Carbon Nucleophiles containing N, S, P, or Bi substituents [21]
    Miscellaneous Additions [22]
  Enolization and Related Reactions [23]
    Enolates [26]
  Oxidation and Reduction of Carbonyl Compounds [27]
    Regie-, Enantio-, and Diastereo-selective Redox Reactions [27]
    Other Redox Reactions [28]
  Other Reactions [29]
  References [31]
CHAPTER 2 Reactions of Carboxylic, Phosphoric and Sulfonic Acids and their Derivatives W. J. SPILLANE
Chemistry Department, National University of Ireland, Galway, Ireland
  Carboxylic acids
    Tetrahedral Intermediates [38]
    Intermolecular Catalysis and Reactions [42]
      Reactions in Hydroxylic Solvents [42]
        (a) General [42]
        (b) Esters [42]
          (i) Formation [42]
          (ii) Transesterification [42]
          (iii) Other reactions [43]
        (c) Lactones and derivatives [46]
        (d) Acids and anhydrides [47]
        (e) Acid halides [50]
        (f) Ureas, carbamates, hydroxylamine, and derivatives [51]
        (g) Amides and anilides [53]
        (h) Lactams [56]
        (i) Non-heterocyclic nitrogen centres [57]
        (j) Other heterocyclic nitrogen centres [58]
    Reactions in Aprotic Solvents [61]
    Intramolecular Catalysis and Neighbouring-group Participation [61]
    Association-prefaced Catalysis [64]
    Metal-ion Catalysis [68]
    Decarboxylation [70]
    Enzymic Catalysis [72]
      General [72]
      Serine Proteinases [73]
      Lipases and (?)-Lactamases [73]
      Other Enzymes [74]
      Catalytic Antibodies [76]
  NON-CARBOXYLIC ACIDS [76]
    Phosphorus-containing Acids [76]
      Phosphates and Phosphonates [76]
      Phosphorus-Nitrogen Centres [78]
      Phosphorus-Oxygen and Phosphorus-Sulfur Centres [79]
      Biologically Important Reactions [81]
    Sulfur-containing Acids [83]
      Sulfur-Oxygen Compounds [83]
      Sulfur-Nitrogen Compounds [85]
      Sulfur-Carbon Compounds and Other Sulfur-containing Functionalities [88]
    Other Acids [90]
    References [90]
CHAPTER 3 Radical Reactions: Part 1 A. I CLARK and R. P. FILIK
Department of Chemistry, University of Warwick
  Introduction [100]
  Rearrangements [100]
    Group Migration [100]
    (?)-Scission (Ring Opening) [101]
    Ring Expansion [103]
  Intramolecular Addition [104]
    Cyclization [104]
    Tandem Reactions [106]
    Radical Annulation [109]
  Fragmentation, Recombination, and Homolysis [109]
  Atom Abstraction Reactions [112]
    Hydrogen Abstraction by Carbon-centred Radicals [112]
    Hydrogen Abstraction by Heteroatom-centred Radicals [113]
    Halogen Abstraction [115]
  Halogenation [116]
  Addition Reactions [117]
    Addition to Alkenes/Alkynes [117]
    Addition to Oxygen-containing Multiple Bonds [119]
    Addition to Nitrogen-containing Multiple Bonds [119]
    Addition to Thiocarbonyl Bonds [119]
  Homolytic Substitution [119]
    Aromatic Substitution [119]
    (?) and Related Reactions [121]
  Reactivity Effects [122]
    Polarity and Philicity [122]
    Stability of Radicals [122]
  Stereoselectivity in Radical Reactions [123]
    Stereoselectivity in Cyclization [123]
    Stereoselectivity of Addition to Alkenes [124]
    Stereoselectivity of Atom Transfer [126]
  Redox Reactions [126]
  Radical Ions [128]
    Anion Radicals [128]
    Cation Radicals [129]
  Peroxides, Peroxyl, and Hydroxyl Radicals [129]
    Peroxides [129]
    Peroxyl Radicals [130]
    Hydroxyl Radical [131]
  References [132]
CHAPTER 4 Radical Reactions: Part 2 A. P. DOBBS AND I N. MARTIN
Chemistry Department, Open University, Milton Keynes
  Structure and Stability [139]
    Carbon-centred Radicals [139]
    Miscellaneous Radicals [141]
  Nitroxides and Spin Trapping [141]
  Oxidation and Reduction [143]
  Electron-transfer Reactions [144]
    Photo-induced Electron Transfers [144]
    Other Electron Transfers [149]
  Radical Cations [151]
  Radical Anions [158]
  Biradicals [160]
  Pyrolysis and Thermolysis [164]
  Photolysis [167]
  Radiolysis [169]
  Autoxidation [171]
  References [171]
CHAPTER 5 Oxidation and Reduction B. G. DAVIS and I A. G. WILLIAMS
Department of Chemistry, Durham University, South Road, Durham DH1 3LE
  Oxidation by Metal Ions and Related Species [179]
    Chromium, Manganese, and Nickel [179]
    Silver, Copper, and Thallium [183]
    Cerium, Cobalt, Vanadium, Molybdenum, Rhenium, Bismuth, Palladium, and Iridium [183]
    Group VIII Metals [186]
  Oxidation by Compounds of Non-metallic Elements [190]
    Nitrogen, Selenium, and Sulfur [190]
    Halogens [191]
  Ozonolysis and Ozonation [193]
  Peracids and Peroxides [194]
  Photo-oxygenation, Singlet Oxygen, and Superoxide [200]
  Atomic Oxygen, Triplet Oxygen, and Autoxidation [203]
  Other Oxidations [204]
  Reduction by Complex Metal Hydrides [204]
  Other Reductions [207]
  References [212]
CHAPTER 6 Carbenes and Nitrenes J. G. KNIGHT
Department of Chemistry, University of Newcastle-upon-Tyne
  Reviews [221]
  Structure and Reactivity [221]
  Generation [225]
  Addition [228]
  Insertion and Abstraction [229]
  Rearrangement [231]
  Nitrenium Ions [234]
  Nucleophiles and Electrophiles [234]
  Silylenes and Germylenes [237]
  References [237]
CHAPTER 7 Nucleophilic Aromatic Substitution M. R. CRAMPTON
Department of Chemistry, University of Durham
  General [241]
  The (?)Ar Mechanism [242]
  Heterocyclic Systems [250]
  Meisenheimer and Related Adducts [252]
  Benzyne and Related Intermediates [254]
  References [254]
CHAPTER 8 Electrophilic Aromatic Substitution R. G. COOMBES
Chemistry Unit, Institute of Physical and Environmental Sciences, Brunei University, Uxbridge
  General [259]
  Halogenation [261]
  Nitration [262]
  Alkylation, Acylation, and Related Reactions [264]
  Other Reactions [267]
  References [269]
CHAPTER 9 Carbocations R. A. Cox
Department of Chemistry, University of Toronto, Canada
  Introduction [273]
  Simple Carbocations [274]
  Benzyl Cations [275]
  Benzhydryl, Trityl, and Fluorenyl Cations [276]
  Acylium Ions [277]
  Oxonium Ions [278]
  Carbocations Containing Sulfur [279]
  Carbocations Containing Silicon [279]
  Fluorinated Carbocations [281]
  Other Destabilized Carbocations [283]
  Carbocations Containing Other Heteroatoms [284]
  Carbocations in Zeolites [285]
  Allylic Systems [285]
  Vinyl and Aryl Cations [285]
  Arenium and Nitrenium Ions [286]
  Aromatic Systems [288]
  Dications [289]
  Polycyclic Systems [291]
  Bridged Systems [292]
  References [293]
CHAPTER 10 Nucleophilic Aliphatic Substitution J. SHORTER
Department of Chemistry, University of Hull, Hull (?) (?)RX
  Vinylic Systems [299]
  Allylic and Other Unsaturated Systems [301]
  Norbornyl System [302]
  Miscellaneous Polycyclic Systems [302]
  Epoxide Reactions [305]
  Other Small Rings [307]
  Substitution at Elements Other than Carbon [308]
  Intramolecular Substitution [310]
  Anchimeric Assistance [311]
  Ambident Nucleophiles [311]
  Isotope Effects [311]
  Gas-phase Reactions [312]
  Radical Processes [315]
  Medium Effects [316]
  Phase-transfer Catalysis and Other Intermolecular Effects [318]
  Structural Effects [319]
    Correlation Analysis by the Hammett Equation and other LFERs [319]
    Nucleophilicity and Leaving-group Effects [321]
  Miscellaneous Studies (Mainly Kinetic) [322]
  Acknowledgement [322]
  References [323]
CHAPTER 11 Carbanions and Electrophilic Aliphatic Substitution A. C. KNIPE
School of Applied Biological and Chemical Sciences, University of Ulster, Coleraine
  Carbanion Structure and Stability [327]
  Carbanion Reactions [330]
    Enolates and Related Species [330]
    Heteroatom-stabilized Species [339]
    Organometallic Species [341]
  Proton-transfer Reactions [344]
  Miscellaneous [351]
  Electrophilic Aliphatic Substitution [355]
  References [356]
CHAPTER 12 Elimination Reactions A. C. KNIPE
School of Applied Biological and Chemical Sciences, University of Ulster, Coleraine
  E1cB Mechanisms [361]
  E2 Mechanisms [365]
  Solvolytic Reactions [367]
  Pyrolytic Reactions [371]
    Cycloreversion with Nitrogen Extrusion [371]
    Other Cycloreversions [372]
    Acid Derivatives [375]
    Sulfur Compounds [378]
    Alkyl Halides [378]
    Nitrogen Compounds [379]
    Alcohols [379]
    Other Pyrolytic Reactions [379]
  Reactions Catalysed by Biomolecules [380]
  Elimination Reactions in Synthesis [383]
  Other Reactions [385]
  References [388]
CHAPTER 13 Addition Reactions: Polar Addition P. KOCOVSKY
Department of Chemistry, University of Glasgow, Glasgow G12 8QQ, UK
  Reviews [391]
  Electrophilic Additions [391]
    Halogenation and Related Reactions [393]
    Additions of ArSX, ArSeX, and Related Reactions [397]
    Additions of Hydrogen Halides and Other Acids [397]
    Additions of Electrophilic Carbon [400]
    Additions of Electrophilic Nitrogen and Oxygen [402]
    Additions Initiated by Metals and Metal Ions as Electrophiles [405]
    Miscellaneous Electrophilic Additions [409]
  Nucleophilic Additions [410]
    Additions to Multiple Bonds Conjugated with C=O [410]
    Additions to Multiple Bonds Activated by Other Electron-withdrawing Groups [416]
    Additions of Organometallics to Activated Double Bonds [420]
    Miscellaneous Nucleophilic Additions [422]
  References [424]
CHAPTER 14 Addition Reactions: Cycloaddition N. DENNIS
University of Queensland, GPO Box 6382, Brisbane, Queensland 4067, Australia
  2 + 2-Cycloaddition [429]
  2 + 3-Cycloaddition [435]
  2 + 4-Cycloaddition [446]
  Miscellaneous Cycloadditions [461]
  References [466]
CHAPTER 15 Molecular Rearrangements A. W. MURRAY
Department of Chemistry, University of Dundee
  Aromatic Rearrangements [473]
    Benzene Derivatives [473]
    Heterocyclic Derivatives [484]
  Sigmatropic Rearrangements [496]
    [3,3]-Migrations [496]
    Claisen and related rearrangements [496]
    Cope and related rearrangements [507]
    [2,3]-Migrations [512]
    [1,3]-Migrations [519]
    [1,5]-Migrations [522]
    Miscellaneous [523]
  Electrocyclic Reactions [530]
  Anionic Rearrangements [543]
  Cationic and Related Rearrangements [550]
  Rearrangements in Natural-product Systems [565]
  Rearrangements Involving Electron-deficient Heteroatoms [568]
  Rearrangements Involving Organometallic Compounds [571]
  Rearrangements Involving Ring Opening [577]
  Isomerizations [587]
    Tautomerism [588]
  References [590]
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