6. Acidity and Basicity of Cyclopropanes

  1. Zvi Rappoport
  1. Merle A. Battiste1 and
  2. James M. Coxon2

Published Online: 28 JAN 2005

DOI: 10.1002/0470023449.ch6

Cyclopropyl Group: Volume 1 and Volume 2 (1987)

Cyclopropyl Group: Volume 1 and Volume 2 (1987)

How to Cite

Battiste, M. A. and Coxon, J. M. (1987) Acidity and Basicity of Cyclopropanes, in Cyclopropyl Group: Volume 1 and Volume 2 (1987) (ed Z. Rappoport), John Wiley & Sons, Ltd, Chichester, UK. doi: 10.1002/0470023449.ch6

Editor Information

  1. The Hebrew University, Jerusalem, Israel

Author Information

  1. 1

    University of Florida, Gainesville, Florida, USA

  2. 2

    University of Canterbury, Christchurch, New Zealand

Publication History

  1. Published Online: 28 JAN 2005
  2. Published Print: 28 OCT 1987

Book Series:

  1. PATAI'S Chemistry of Functional Groups

Book Series Editors:

  1. Saul Patai

ISBN Information

Print ISBN: 9780471917380

Online ISBN: 9780470023440

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Summary

This chapter contains sections titled:

  • Introduction

  • Bonding Considerations

  • Acidity

    • General Aspects

    • Cyclopropane and Related Strained Hydrocarbons

    • Substituent Effects on Cyclopropyl Anion Structure and Stability

    • Unsaturated Derivatives of Cyclopropane

      • Cyclopropenes

      • Benzocyclopropene

      • Methylenecyclopropanes

  • Basicity

    • Theoretical Aspects

    • Protonated Cyclopropane

    • Protonated Methylcyclopropane

    • Protonated 1,1,2,2-tetramethylcyclopropane

    • Protonated Nortricyclene

    • Electrophilic Addition and Isomerization Reactions of Cyclopropanes

      • Direction and Rate of Ring-opening Reactions

      • Ring-opening Reactions Inducing Molecular Rearrangements

      • Stereochemistry of Reactions with Electrophiles and Nucleophiles

    • Acid-catalyzed Rearrangements of Cyclopropenes

  • References