Fullerenes: Chemistry and Reactions

Abstract

Foreword. Preface of Chemistry of the 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 C60Hn and C70Hn (n = 2-12). 5.3 Polyhydrofullerenes C60Hn and C70Hn (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 (eta2-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 C60. 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.