Fullerenes - Chemistry And Reactions

In this handbook, the leading experts in the field presents important and fundamental aspects of the organic and organometallic chemistry of fullerenes. Naturally they also cover the applications in material and medicinal science for these fascinating molecules.
Completely self-contained, the book is logically arranged such that information is easy to retrieve, and the style lends itself to effortless reading and to learning more about the chemical properties of this family of molecules.
A definitive "must" for everyone working in this ever-expanding sphere.

Andreas Hirsch was born in Esslingen, Germany, in 1960. He studied chemistry at the University of Tübingen, Germany, where he obtained his PhD in 1990 under Michael Hanack. He has carried out postdoctoral research at the Institute for Polymers and Organic Solids in Santa Barbara, California, with Fred Wudl. In 1991 he subsequently returned to Tübingen as research associate at the Institute for Organic Chemistry. After his Habilitation in 1994 he joined the faculty of the Department of Chemistry at the University of Karlsruhe as a professor. Since October 1995, he has been Full Profes-sor of Organic Chemistry at Friedrich-Alexander-Universität, Erlangen-Nürnberg. Andreas Hirsch's main research activities have been focussed on the development of methodologies for efficient syntheses of exohedral derivatives of fullerenes and the use of such compounds as structural templates and building blocks for supramolecular architectures and nanomaterials. Other research interests are in the area of dendrimers, calixarene conjugates, new alkynes, new types of synthetic lipids and amphiphiles, model compounds for photoinduced charge separation, chemical derivatization and solubilization of carbon nanotubes, including the investigation of their synthetic potential and properties as new materials.

Michael Brettreich was born in Nürnberg, Germany in 1968. He studied chemistry in Erlangen and received his Ph. D. in 2000 in the group of Andreas Hirsch. From 2000 to 2001 he did postdoctoral research in the group of Fred Wudl at the UCLA. His research interests concentrate on the field of chemistry and supramolecular chemistry of fullerenes in particular the design of amphiphilic and watersoluble fullerene derivatives. Currently he holds an administrative position in the Institute for Organic Chemistry in Erlangen.

Foreword.

Preface of “The Chemistry of the Fullerenes” by Andreas Hirsch (1994).

Abbreviations.

1 Parent Fullerenes.

1.1 Fullerenes: Molecular Allotropes of Carbon.

1.2 Discovery of the Fullerenes.

1.3 Fullerene Production.

1.4 Separation and Purification.

1.5 Properties.

References.

2 Reduction.

2.1 Introduction.

2.2 Fulleride Anions.

2.3 Reductive Electrosynthesis.

2.4 Reduction with Metals.

2.5 Reduction with Organic Donor Molecules.

References.

3 Nucleophilic Additions.

3.1 Introduction.

3.2 Addition of Carbon Nucleophiles.

3.3 Addition of Amines.

3.4 Addition of Hydroxide and Alkoxides.

3.5 Addition of Phosphorus Nucleophiles.

3.6 Addition of Silicon and Germanium Nucleophiles.

3.7 Addition of Macromolecular Nucleophiles – Fullerene Polymers.

References.

4 Cycloadditions.

4.1 Introduction.

4.2 [4+2] Cycloadditions.

4.3 [3+2] Cycloadditions.

4.4 [2+2] Cycloadditions.

4.5 [2+1] Cycloadditions.

References.

5 Hydrogenation.

5.1 Introduction.

5.2 Oligohydrofullerenes C₆₀H_n and C₇₀H_n (n = 2–12).

5.3 Polyhydrofullerenes C₆₀H_n and C₇₀H_n (n = 14–60).

References.

6 Radical Additions.

6.1 Introduction.

6.2 ESR Investigations of Radical Additions.

6.3 Addition of Tertiary Amines.

6.4 Photochemical Reaction with Silanes.

6.5 Metalation of C₆₀ with Metal-centered Radicals.

6.6 Addition of bis(Trifluoromethyl)nitroxide.

References.

7 Transition Metal Complex Formation.

7.1 Introduction.

7.2 (η²-C₆₀) Transition Metal Complexes.

7.3 Multinuclear Complexes of C₆₀.

7.4 Hydrometalation Reactions.

7.5 Organometallic Polymers of C₆₀.

References.

8 Oxidation and Reactions with Electrophiles.

8.1 Introduction.

8.2 Electrochemical Oxidation of C₆₀ and C₇₀.

8.3 Oxygenation.

8.4 Osmylation.

8.5 Reactions with Strong Oxidizing Reagents and Acids.

8.6 Reactions with Lewis Acids and Fullerylation of Aromatics and Chloroalkanes.

References.

9 Halogenation.

9.1 Introduction.

9.2 Fluorination.

9.3 Chlorination.

9.4 Bromination.

9.5 Reaction with Iodine.

References.

10 Regiochemistry of Multiple Additions.

10.1 Introduction.

10.2 Addition of Segregated Addends – The Inherent Regioselectivity.

10.3 Concepts for Regio- and Stereoselective Multiple Functionalization of C^₆₀.

References.

11 Cluster Modified Fullerenes.

11.1 Introduction.

11.2 Cluster Opened Fullerene Derivatives.

11.3 Quasi-fullerenes.

11.4 Outlook.

References.

12 Heterofullerenes.

12.1 Introduction.

12.2 Synthesis of Nitrogen Heterofullerenes from Exohedral Imino Adducts of C₆₀ and C₇₀.

12.3 Chemistry of Azafullerenes.

12.4 Outlook.

References.

13 Chemistry of Higher Fullerenes.

13.1 Introduction.

13.2 Exohedral Reactivity Principles.

13.3 Adducts of C₇₀.

13.4 Adducts of C₇₆, C₇₈ and C₈₄.

References.

14 Principles and Perspectives of Fullerene Chemistry.

14.1 Introduction.

14.2 Reactivity.

14.3 Regiochemistry of Addition Reactions.

14.4 Aromaticity of Fullerenes.

14.5 Seven Principles of Fullerene Chemistry: a Short Summary.

14.6 The Future of Fullerene Chemistry.

14.7 Fullerenes as Building Blocks for Molecular Engineering (Nanotechnology) and Practical Applications.

References.

Subject Index.