The Chemistry of Organolithium Compounds

The Chemistry of Organolithium Compounds

1st Edition - January 1, 1974

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  • Author: B. J. Wakefield
  • eBook ISBN: 9781483278704

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The Chemistry of Organolithium Compounds is a comprehensive review of the status of organolithium compound chemistry. This book is composed of four parts and nineteen chapters that particularly describe the reactions involving these compounds The first part highlights the constitution of organolithium compounds, specifically in the absence and presence of electron donors, as well as the configurational stability of these compounds. The second part deals with their preparation from organic halides and lithium metal involving metallation and metal-halogen exchange, while the third part focuses on their organic synthesis. The fourth part considers the synthesis of organometallic compound derivatives from main group and transition metals. This book will prove useful to organic chemists and organic chemistry researchers.

Table of Contents

  • Preface


    Part I. The Constitution of Organolithium Compounds

    1. The Constitution of Organolithium Compounds

    1.1. Constitution in the Absence of Electron Donors

    1.2. Constitution in the Presence of Electron Donors

    1.3. Structure of Benzylic and Ally Lie Organolithium Compounds

    1.4. Configurational Stability of Organolithium Compounds

    1.5. Effect of Structure and Coordination On Reactivity

    References for Part I

    Part II. The Preparation of Organolithium Compounds

    2. Preparation from Organic Halides and Lithium Metal

    3. Preparation by Metallation

    3.1. Metallation of Hydrocarbon Acids

    3.2. Metallation of "Active Methylene" Groups ("α-Metallation")

    3.3. Metallation of Substituted Aromatic Compounds

    3.4. Metallation of Heterocyclic Aromatic Compounds

    3.5. Metallation of Metallocenes, Carboranes and Related Compounds

    4. Preparation by Metal-Halogen Exchange

    4.1. Preparation of Aryl-Lithium Compounds by Metal-Halogen Exchange

    4.2. Preparation of Heterocyclic Aromatic Lithium Compounds by Metal-Halogen Exchange

    4.3. Preparation of Alkyl- and Alkenyl-Lithium Compounds by Compounds by Metal-Halogen Exchange

    5. Miscellaneous Methods for Preparing Organolithium Compounds

    5.7. Transmetallation

    5.2. One-Electron Transfers from Lithium Metal

    5.3. Other Methods of Preparation

    6. Detection and Estimation of Organolithium Compounds

    6.1. Detection

    6.2. Estimation

    References for Part II

    Part III. Organolithium Compounds in Organic Synthesis

    7. Addition of Organolithium Compounds to Carbon-Carbon Multiple Bonds

    7.1. Addition to Unconjugated Carbon-Carbon Multiple Bonds

    7.2. Addition to Conjugated Carbon-Carbon Multiple Bonds

    7.3. Polymerisation Initiated by Organolithium Compounds

    7.4. Addition to Aromatic Rings

    8. Addition of Organolithium Compounds to Carbon-Nitrogen Multiple Bonds

    8.1. Addition to Imines

    8.2. Addition to Nitrogen Heterocyclic Aromatic Compounds

    8.3. Addition to Nitriles and Isonitriles

    9. Addition of Organolithium Compounds to Carbon-Oxygen and Carbon-Sulphur Multiple Bonds

    9.1. Addition to Free and Coordinated Carbon Monoxide

    9.2. Addition to Carbon Dioxide and Metal Carboxylates

    9.3. Addition to Isocyanates, Isothiocyanates and Ketens

    9.4. Addition to Aldehydes and Ketones

    9.5. Addition to Acyl Derivatives

    10. Alkylation With Organolithium Compounds

    10.1. Alkylation of Organic Halides

    10.2. Displacement of Groups Other than Halogen

    11. Protonation of Organolithium Compounds

    11.1. Mechanism of Protonation of Organolithium Compounds

    11.2. Synthesis of Lithium Alkoxides and Amides

    11.3. Indirect Reduction of Organic Halides

    11.4. Hydrogen Isotopic Labelling via Organolithium Compounds

    12. Organolithium Compounds as Precursors for Reactive Intermediates

    12.1. Carbenes

    12.2. Arynes

    12.3. Cycloalkynes and Cycloallenes

    12.4. Ylides

    13. Reactions of Organolithium Compounds With Non-Metallic Elements

    13.1. Hydrogen

    13.2. Oxygen

    13.3. Sulphur, Selenium and Tellurium

    13.4. Halogens

    14. Cleavage of Ethers and Related Compounds by Organolithium Compounds

    14.1. Acyclic Ethers and Cyclic Ethers with Five-Membered Or Larger Rings

    14 2. Epoxides and Episulphides

    14.3. Oxetans and Thietans

    14.4. Acetals and Related Compounds

    15. Pyrolysis, Photolysis, Rearrangement and Ring-Opening of Organolithium Compounds

    15.1. Pyrolysis

    15.2. Photolysis

    15.3. Rearrangement

    15.4. Ring-Opening

    16. Miscellaneous Reactions of Organolithium Compounds

    References for Part III

    Part IV. Organolithium Compounds in Organometallic Synthesis

    17. Synthesis of Derivatives of Main Group Metals

    17.1. General Principles

    17.2. Group I

    17.3. Group II

    17.4. Group III

    17.5. Group IV

    17.6. Group V

    17.7. Selenium and Tellurium

    18. Synthesis of Derivatives of Transition Metals

    18.1. Group IB

    18.2. Group IIIA

    18.3. Group IVA

    18.4. Group VA

    18.5. Group VIA

    18.6. Group VIIA

    18.7. Group VIII

    19. Organometallic Compounds Containing Lithium-Metal Bonds

    19.1. Group IV metal Compounds

    19.2. Group V metal Compounds

    19.3. Group VI: Selenyl- and Telluryl-Lithium Compounds (Lithium Selenides and Tellurides)

    References for Part IV


Product details

  • No. of pages: 348
  • Language: English
  • Copyright: © Pergamon 1974
  • Published: January 1, 1974
  • Imprint: Pergamon
  • eBook ISBN: 9781483278704

About the Author

B. J. Wakefield

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