Fullerenes chemistry and reactions 2005 hirsch brettreich

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Fullerenes   chemistry and reactions 2005   hirsch  brettreich

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... Aldol Reactions Volumes 2004 ISBN 3-527-30714-1 Andreas Hirsch, Michael Brettreich Fullerenes Chemistry and Reactions Authors: Prof Dr Andreas Hirsch Dr Michael Brettreich Department of Organic Chemistry. ..Andreas Hirsch, Michael Brettreich Fullerenes Chemistry and Reactions Andreas Hirsch Michael Brettreich Fullerenes Further Reading from WILEY-VCH S... In Fullerenes – Chemistry and Reactions Professor Hirsch has expanded the original chapters to 14 The new chapters cover halogenation (Chap 9), regiochemistry (Chap 10), cluster modified fullerenes

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  • Fullerenes

    • Foreword

    • Preface

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

    • Contents

    • Abbreviations

    • 1 Parent Fullerenes

      • 1.1 Fullerenes: Molecular Allotropes of Carbon

      • 1.2 Discovery of the Fullerenes

      • 1.3 Fullerene Production

        • 1.3.1 Fullerene Generation by Vaporization of Graphite

          • 1.3.1.1 Resistive Heating of Graphite

          • 1.3.1.2 Arc Heating of Graphite

          • 1.3.1.3 Solar Generators

          • 1.3.1.4 Inductive Heating of Graphite and Other Carbon Sources

        • 1.3.2 Fullerene Synthesis in Combustion

        • 1.3.3 Formation of Fullerenes by Pyrolysis of Hydrocarbons

        • 1.3.4 Generation of Endohedral Fullerenes

        • 1.3.5 Total Synthesis Approaches

        • 1.3.6 Formation Process

      • 1.4 Separation and Purification

      • 1.5 Properties

        • 1.5.1 Structures

        • 1.5.2 Physical and Spectroscopic Properties

      • References

    • 2 Reduction

      • 2.1 Introduction

      • 2.2 Fulleride Anions

      • 2.3 Reductive Electrosynthesis

        • 2.3.1 Electrocrystallization

        • 2.3.2 Electrophilic Additions to Fulleride Anions

      • 2.4 Reduction with Metals

        • 2.4.1 Alkali Metal Fullerides

          • 2.4.1.1 Generation in Solution and Quenching Experiments

          • 2.4.1.2 Synthesis and Properties of Alkali Metal Fulleride Solids

        • 2.4.2 Alkaline Earth Metal Fullerides

        • 2.4.3 Reduction with Mercury

      • 2.5 Reduction with Organic Donor Molecules

      • References

    • 3 Nucleophilic Additions

      • 3.1 Introduction

      • 3.2 Addition of Carbon Nucleophiles

        • 3.2.1 Hydroalkylation and Hydroarylation of C(60) and C(70)

        • 3.2.2 Cyclopropanation of C(60) and C(70)

        • 3.2.3 Addition of Cyanide

      • 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

        • 4.3.1 Addition of Diazomethanes, Diazoacetates and Diazoamides

        • 4.3.2 Addition of Azides

        • 4.3.3 Addition of Trimethylenemethanes

        • 4.3.4 Addition of Azomethine Ylides

        • 4.3.5 Addition of Nitrile Oxides and Nitrile Imines

        • 4.3.6 Addition of Sulfinimides and Thiocarbonyl Ylides

        • 4.3.7 Addition of Carbonyl Ylides

        • 4.3.8 Addition of Nitrile Ylides and Isonitriles

        • 4.3.9 Addition of Disiliranes

      • 4.4 [2+2] Cycloadditions

        • 4.4.1 Addition of Benzyne

        • 4.4.2 Addition of Enones

        • 4.4.3 Addition of Electron-rich Alkynes and Alkenes

        • 4.4.4 Addition of Ketenes and Ketene Acetals

        • 4.4.5 Addition of Quadricyclane

        • 4.4.6 Photodimerization of C(60)

      • 4.5 [2+1] Cycloadditions

        • 4.5.1 Addition of Carbenes

        • 4.5.2 Addition of Nitrenes

        • 4.5.3 Addition of Silylenes

      • References

    • 5 Hydrogenation

      • 5.1 Introduction

      • 5.2 Oligohydrofullerenes C(60)H(n) and C(70)H(n) (n = 2–12)

        • 5.2.1 Hydrogenation via Hydroboration and Hydrozirconation

        • 5.2.2 Reduction with Reducing Metals (Zn/Cu)

        • 5.2.3 Hydrogenation with Hydrazine and with Organic Reducing Agents

        • 5.2.4 Theoretical Investigations

      • 5.3 Polyhydrofullerenes C(60)H(n) and C(70)H(n) (n = 14–60)

        • 5.3.1 Birch–Hückel Reduction

        • 5.3.2 Reduction with Zn/HCl

        • 5.3.3 Transfer Hydrogenation of C(60) and C(70)

        • 5.3.4 Reduction with Molecular Hydrogen

        • 5.3.5 Theoretical Investigations

      • References

    • 6 Radical Additions

      • 6.1 Introduction

      • 6.2 ESR Investigations of Radical Additions

        • 6.2.1 Addition of Single Radicals

        • 6.2.2 Multiple Radical Additions

      • 6.3 Addition of Tertiary Amines

      • 6.4 Photochemical Reaction with Silanes

      • 6.5 Metalation of C(60) with Metal-centered Radicals

      • 6.6 Addition of bis(Trifluoromethyl)nitroxide

      • References

    • 7 Transition Metal Complex Formation

      • 7.1 Introduction

      • 7.2 (η(2)-C(60)) Transition Metal Complexes

      • 7.3 Multinuclear Complexes of C(60)

      • 7.4 Hydrometalation Reactions

      • 7.5 Organometallic Polymers of C(60)

      • References

    • 8 Oxidation and Reactions with Electrophiles

      • 8.1 Introduction

      • 8.2 Electrochemical Oxidation of C(60) and C(70)

      • 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

        • 9.2.1 Direct Fluorination with F(2)

        • 9.2.2 Fluorination with Noble Gas Fluorides and Halogen Fluorides

        • 9.2.3 Reactions with Metal Fluorides

        • 9.2.4 Reactions of Fluorofullerenes

      • 9.3 Chlorination

        • 9.3.1 Synthesis and Properties of Chlorofullerenes

        • 9.3.2 Reactions of Chlorofullerenes

      • 9.4 Bromination [73]

      • 9.5 Reaction with Iodine

      • References

    • 10 Regiochemistry of Multiple Additions

      • 10.1 Introduction

      • 10.2 Addition of Segregated Addends – The Inherent Regioselectivity

        • 10.2.1 Subsequent Cycloadditions to [6,6]-double Bonds

        • 10.2.2 Adducts with an Inherently Chiral Addition Pattern

        • 10.2.3 Vinylamine Mode

        • 10.2.4 Cyclopentadiene Mode

      • 10.3 Concepts for Regio- and Stereoselective Multiple Functionalization of C(60)

        • 10.3.1 Template Mediation Approaches

          • 10.3.1.1 T(h)-Symmetrical Hexakisadducts

          • 10.3.1.2 Mixed Hexakisadducts

        • 10.3.2 Topochemically Controlled Solid-state Reactions

        • 10.3.3 Tether-directed Remote Functionalization of C(60)

          • 10.3.3.1 Higher Adducts with the Addends Bound in Octahedral Sites

          • 10.3.3.2 Multiple Cyclopropanation of C(60) by Tethered Malonates

          • 10.3.3.3 Highly Regioselective Cyclopropanation of C(60) with Cyclo-[n]-alkylmalonates

          • 10.3.3.4 Double Diels–Alder Tethers

          • 10.3.3.5 Other Bisfunctional Tethers

      • References

    • 11 Cluster Modified Fullerenes

      • 11.1 Introduction

      • 11.2 Cluster Opened Fullerene Derivatives

        • 11.2.1 “Fulleroids”: Bridged Adducts with Open Transannular Bonds

        • 11.2.2 Ring-enlargement Reactions of Bisfulleroids

        • 11.2.3 Cluster Opened Lactams, Ketolactams and Lactones

      • 11.3 Quasi-fullerenes

      • 11.4 Outlook

      • References

    • 12 Heterofullerenes

      • 12.1 Introduction

      • 12.2 Synthesis of Nitrogen Heterofullerenes from Exohedral Imino Adducts of C(60) and C(70)

        • 12.2.1 Synthesis of bis(Aza[60]fullerenyl) (C(59)N)(2)

        • 12.2.2 Synthesis of bis(Aza[70]fullerenyl) (C(69)N)(2)

      • 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 C(70)

        • 13.3.1 Monoadducts

        • 13.3.2 Multiple Adducts

      • 13.4 Adducts of C(76), C(78) and C(84)

      • References

    • 14 Principles and Perspectives of Fullerene Chemistry

      • 14.1 Introduction

      • 14.2 Reactivity

        • 14.2.1 Exohedral Reactivity

        • 14.2.2 Endohedral Reactivity

      • 14.3 Regiochemistry of Addition Reactions

        • 14.3.1 Bond Length Alternation – Preferred Additions to [6,6]-Double Bonds

        • 14.3.2 1,2-Additions with Preferred e- and cis-1 Modes: the trans-1 Effect

        • 14.3.3 Vinyl Amine Mode

        • 14.3.4 Cyclopentadiene Mode

        • 14.3.5 Further Modes

      • 14.4 Aromaticity of Fullerenes

        • 14.4.1 Structural Criteria

        • 14.4.2 Energetic Criteria

        • 14.4.3 Reactivity Criteria

        • 14.4.4 Magnetic Criteria

        • 14.4.5 2(N + 1)(2)-Rule for Spherical Aromaticity

      • 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

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