10. Conjugative and Substituent Properties of the Cyclopropyl Group

  1. Zvi Rappoport
  1. Thomas T. Tidwell

Published Online: 28 JAN 2005

DOI: 10.1002/0470023449.ch10

Cyclopropyl Group: Volume 1 and Volume 2 (1987)

Cyclopropyl Group: Volume 1 and Volume 2 (1987)

How to Cite

Tidwell, T. T. (1987) Conjugative and Substituent Properties of the Cyclopropyl Group, in Cyclopropyl Group: Volume 1 and Volume 2 (1987) (ed Z. Rappoport), John Wiley & Sons, Ltd, Chichester, UK. doi: 10.1002/0470023449.ch10

Editor Information

  1. The Hebrew University, Jerusalem, Israel

Author Information

  1. Department of Chemistry, University of Toronto, Scarborough Campus, Scarborough, Ontario, Canada M1C 1A4

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

  • Substituent Properties of Cyclopropyl

    • Methods of Study

    • Cyclopropyl-substituted Acids and Bases

    • Conformational Dependence of Cyclopropyl Conjugation

    • X-ray Structure Determination of Cyclopropyl Compounds

    • Thermochemical Measurements

    • Substituent Parameters

    • Charge Transfer and Ionization Potentials

    • ρ+ Values

    • Transmission of Substituent Effects

  • Heteroatom-substituted Cyclopropanes

    • General Survey

    • Metal Substituents (Groups I–III)

    • Group IV Metalloid Substituents

    • Nitrogen and Phosphorous Substituents

    • Oxygen and Sulfur Substituents

    • Halogen Substituents

  • Carbon-substituted Cyclopropanes

    • Saturated Carbon Groups

    • Cyclopropylalkenes

    • Cyclopropylarenes

    • Cyclopropyl Carbonyl Derivatives

    • Cyclopropylalkynes

    • Cyclopropyl Cyanide

  • Cyclopropylcarbinyl Carbocations

    • equation image

    • Substituted Cyclopropylcarbinyl Cations

    • Structure and Conformation of Cyclopropylcarbinyl Cations

    • Conformationally Restricted Cyclopropylcarbinyl Cations

      • Solvolysis Studies

      • Inductive Effect of Cyclopropyl

      • Long-lived Carbocations

      • Nortricyclyl Cations

    • Phenonium Ions

    • Cyclopropyl-substituted Vinyl Cations

    • Electrophilic Aromatic Substitution of Cyclopropylarenes

    • Homoconjugated Cyclopropyl Cations

    • Thermochemistry of Cyclopropyl-substituted Cations

    • The Relative Conjugating Ability of c-Pr, Ph and Me

  • Cyclopropyl-substituted Reactive Intermediates

    • Cyclopropylcarbinyl Radicals

    • Cyclopropylcarbinyl Anions

    • Cyclopropylcarbenes

    • Cyclopropyl Substituent Effects on Additions to Alkenes

    • Reactions on the Cyclopropyl Ring

      • Cyclopropyl Cations

      • Cyclopropyl Anions

      • Cyclopropyl Radicals

    • Other Cyclopropylcarbinyl Cation Systems

  • Conclusion

  • References