23. The Chemistry of Cyclopropanones

  1. Zvi Rappoport
  1. Harry H. Wasserman,
  2. Donald R. Berdahl and
  3. Ta-Jung Lu

Published Online: 28 JAN 2005

DOI: 10.1002/0470023449.ch23

Cyclopropyl Group: Volume 1 and Volume 2 (1987)

Cyclopropyl Group: Volume 1 and Volume 2 (1987)

How to Cite

Wasserman, H. H., Berdahl, D. R. and Lu, T.-J. (1987) The Chemistry of Cyclopropanones, in Cyclopropyl Group: Volume 1 and Volume 2 (1987) (ed Z. Rappoport), John Wiley & Sons, Ltd, Chichester, UK. doi: 10.1002/0470023449.ch23

Editor Information

  1. The Hebrew University, Jerusalem, Israel

Author Information

  1. Department of Chemistry, Yale University, New Haven, Connecticut 06511, USA

  1. Corporate Research and Development, General Electric Company, P.O. Box 8, Schenectady, N.Y., USA, 12301

  2. Department of Chemistry, Yale University, New Haven, Connecticut 06511, USA

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

  • Preparation of Cyclopropanones and Their Precursors

    • Diazoalkane–Ketene Reactions

    • Photochemical Processes

    • Ring-closure by Dehalogenation or Dehydrohalogenation

    • The Allene Oxide-cyclopropanone Rearrangement

  • Physical Properties of Cyclopropanones

    • Microwave Spectra

    • Electronic Absorption Spectra (UV and ORD)

    • Nuclear Magnetic Resonance Spectra

  • Theoretical Studies

  • Reactions of Cyclopropanones

    • Additions to the Carbonyl Group

      • Polymerization

      • Addition of Water, Alcohols and Acids

      • Reactions with Amines

      • Other Carbonyl Addition Reactions

    • Decarbonylation

    • Ring-opening by C(2)-C(3) Bond Rupture

    • Ring-opening and Ring-expansion Reactions 1480

      • β-lactams and Cyclobutanones

      • Ring-opening Under Basic Conditions

      • Ring-opening Under Neutral and Acidic Conditions

    • Cyclopropanone Derivatives as Homoenolates

    • Thermal and Photochemical Reactions

    • Oxidative Cleavage of Cyclopropanones

    • Cycloaddition Reactions

  • 1,1-Disubstituted Cyclopropanone Equivalents

    • Carbinol Amines

    • Preparation of Other 1,1-disubstituted Cyclopropanones 1495

      • Carbene Addition to Olefins

      • Cyclization Procedures

      • 1,3-displacement Reactions

      • Miscellaneous

  • Reactions of Substituted Cyclopropanone Equivalents

    • Ring-opening Reactions

    • Other Substitution Processes

    • Cycloaddition Reactions

  • Cyclopropanones in Synthesis

  • Biological Aspects of Cyclopropanone Chemistry

  • References