The Chemistry of Organolithium Compounds

1st Edition - January 1, 1974
Author: B. J. Wakefield
Language: English
eBook ISBN:
9 7 8 - 1 - 4 8 3 2 - 7 8 7 0 - 4

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… Read more

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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.

Preface

Abbreviations

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

Index