Chapter 13. Reduction of Carbon-rich Compounds

  1. Prof. Michael M. Haley2 and
  2. Prof. Rik R. Tykwinski3
  1. Tamar Sternfeld and
  2. Mordecai Rabinovitz

Published Online: 13 JUN 2006

DOI: 10.1002/3527607994.ch13

Carbon-Rich Compounds: From Molecules to Materials

Carbon-Rich Compounds: From Molecules to Materials

How to Cite

Sternfeld, T. and Rabinovitz, M. (2006) Reduction of Carbon-rich Compounds, in Carbon-Rich Compounds: From Molecules to Materials (eds M. M. Haley and R. R. Tykwinski), Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim, FRG. doi: 10.1002/3527607994.ch13

Editor Information

  1. 2

    Department of Chemistry, University of Oregon, Eugene, Oregon 97403-1253, USA

  2. 3

    Department of Chemistry, University of Alberta, Edmonton, Alberta, T6G 2G2, Canada

Author Information

  1. Department of Organic Chemistry, The Hebrew University of Jerusalem, Givat Ram, Jerusalem, 91904, Israel

Publication History

  1. Published Online: 13 JUN 2006
  2. Published Print: 6 FEB 2006

ISBN Information

Print ISBN: 9783527312245

Online ISBN: 9783527607990

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Keywords:

  • reduction of carbon-rich compounds;
  • electron transfer methods;
  • monocyclic π-conjugated anions;
  • annulenes;
  • reduction of nonplanar polycyclic aromatic hydrocarbons;
  • corannulene;
  • reduced fullerenes;
  • anions of C60;
  • anion of C70;
  • fullerene derivatives

Summary

This chapter contains sections titled:

  • Introduction

  • Electron Transfer Methods and Detection of the Products

    • Reduction via Alkali Metals

    • The Application of Electron Shuttles

    • Potassium Graphite Intercalates as Reducing Agents

    • Electrochemical Studies

    • Ion Solvation Equilibria in π-Conjugated Reduced Systems

    • Magnetic Resonance Spectroscopy – Tool of Choice for the Study of Reduced Carbon-rich Compounds

      • NMR

      • EPR

  • Monocyclic π-Conjugated Anions

    • Annulenes: General

    • “Classical Annulenes”

      • Cyclooctatetraene–[8]Annulene

      • [12]Annulene

      • [16]Annulene

      • [18]Annulene

    • Dehydroannulenes

    • Cyclophanes

  • Reduction of Nonplanar Polycyclic Aromatic Hydrocarbons

    • Nonplanar PAHs

    • PAHs with Five-membered Rings

      • Corannulene

      • Reduction of Corannulene with Lithium

      • Reduction of Corannulene with Different Alkali Metals

      • Substituted Corannulenes

      • Extended Corannulenes

    • Strain in PAHs: The Story of Curved Pyrene

      • First Reduction Process – Dimerization

      • The Second Reduction Stage

  • Reduced Fullerenes

    • General

    • Reduction Stages of Fullerenes

      • Anions of C60

      • Anions of C70

      • Reduced Higher Fullerenes

    • The Aromatic Character of Reduced Fullerenes

      • Endohedral Helium in Fullerenes – an Internal Probe

      • 13C NMR of Reduced Fullerenes

      • Methylene Bridged Fullerenes – an External Probe

    • Fullerene Derivatives

      • Metallofullerene Complexes

    • Nanotubes

  • Conclusions

  • Experimental: Selected Procedures

    • Reduction with Li and K

    • Quench Reaction with Water

    • Reduction with C8K