Advanced Organic Chemistry

1. Front Matter

   Pages i-xxviii

   PDF

2. Alkylation of Nucleophilic Carbon. Enolates and Enamines

   • Francis A. Carey, Richard J. Sundberg

   Pages 1-54

3. Reactions of Carbon Nucleophiles with Carbonyl Groups

   • Francis A. Carey, Richard J. Sundberg

   Pages 55-120

4. Functional Group Interconversion by Nucleophilic Substitution

   • Francis A. Carey, Richard J. Sundberg

   Pages 121-165

5. Electrophilic Additions to Carbon-Carbon Multiple Bonds

   • Francis A. Carey, Richard J. Sundberg

   Pages 167-218

6. Reduction of Carbonyl and Other Functional Groups

   • Francis A. Carey, Richard J. Sundberg

   Pages 219-281

7. Cycloadditions, Unimolecular Rearrangements, and Thermal Eliminations

   • Francis A. Carey, Richard J. Sundberg

   Pages 283-363

8. Organometallic Compounds of Group I and II Metals

   • Francis A. Carey, Richard J. Sundberg

   Pages 365-400

9. Reactions Involving the Transition Metals

   • Francis A. Carey, Richard J. Sundberg

   Pages 401-441

10. Carbon-Carbon Bond-Forming Reactions of Compounds of Boron, Silicon, and Tin

    • Francis A. Carey, Richard J. Sundberg

    Pages 443-492

11. Reactions Involving Highly Reactive Electron-Deficient Intermediates

    • Francis A. Carey, Richard J. Sundberg

    Pages 493-569

12. Aromatic Substitution Reactions

    • Francis A. Carey, Richard J. Sundberg

    Pages 571-614

13. Oxidations

    • Francis A. Carey, Richard J. Sundberg

    Pages 615-675

14. Multistep Syntheses

    • Francis A. Carey, Richard J. Sundberg

    Pages 677-761

15. Back Matter

    Pages 763-800

    PDF

The main theme of Part B is the description of synthetically useful reactions and the illustration of their application. We have attempted to update the material to reflect the most important advances in synthetic methodology. Because of the extensive developments in the use of organic derivatives of transition metals, as well as of silicon and tin, we have separated the organometallic material into three chapters. Chapter 7 emphasizes organolithium and organomagnesium chemistry and also considers the group lIB metals. Transition metal chemistry is discussed in Chapter 8, with emphasis on copper and palladium intermediates. In Chapter 9, the carbon-carbon bond-forming reactions of organoboranes, silanes, and stannanes are discussed. The increased importance of free-radical reactions in synthesis has led to the incorporation of a section on radical reactions into Chapter 10, in which carbocations, carbenes, and nitrenes are also discussed. Certainly a major advance in synthetic chemistry during the 1980s was the development of methods for enantioselective synthesis. We have increased the level of attention to stereochemistry in the discussion of many reactions. In areas in which new stereoselective methods have been well developed, such as in aldol condensa­ tions, hydroboration, catalytic reduction, and epoxidation, we discuss these methods. The final chapter discusses some of the general issues which must be addressed in multistep synthesis and provides some illustrative syntheses which can provide the basis for more detailed study of this aspect of synthetic chemistry.

• metals
• organic chemistry
• synthesis

• University of Virginia, Charlottesville, USA

  Francis A. Carey, Richard J. Sundberg

Policies and ethics