19. Bicyclo[1.1.0]Butane

  1. Zvi Rappoport
  1. Shmaryahu Hoz

Published Online: 28 JAN 2005

DOI: 10.1002/0470023449.ch19

Cyclopropyl Group: Volume 1 and Volume 2 (1987)

Cyclopropyl Group: Volume 1 and Volume 2 (1987)

How to Cite

Hoz, S. (1987) Bicyclo[1.1.0]Butane, in Cyclopropyl Group: Volume 1 and Volume 2 (1987) (ed Z. Rappoport), John Wiley & Sons, Ltd, Chichester, UK. doi: 10.1002/0470023449.ch19

Editor Information

  1. The Hebrew University, Jerusalem, Israel

Author Information

  1. Bar-Ilan University, Ramat-Gan, Israel

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

  • Structure and Bonding

    • Structure

    • Bonding

    • Deformation Densities

    • The Nature of the Central Bond

    • The HOMO of Bicyclobutane

    • Strain in Bicyclobutane

    • Molecular Distortions

    • Orbital Interactions with External Fragments

  • Structure and Bonding Effects on Reactivity

  • Synthesis

    • Classification

    • Synthetic Routes

      • Case A

      • Case B

      • Case C

      • Case D

      • Case E

      • Case F

  • Reactions of Bicyclobutane

    • Electrophilic Additions

      • Acid-catalyzed Additions

      • Addition of Halogens and Mercuric Salts

      • Mechanism

    • Reactions with Double Bonds

    • Reactions with Nucleophiles

    • Radical Reactions

      • Addition to the Central Bond

      • Hydrogen Abstraction

      • The Radical Cation of Bicyclobutane

    • Reactions with Carbenes

    • Transition Metal Promoted Rearrangements

      • Substituent Effect

      • Metal Effect

      • Ligand Effect

      • Solvent Effect

      • Reaction Mechanism

    • Thermal Reactions

      • Rearrangement

      • Isomerization

    • Hydrogenation

    • Deprotonation Reactions

    • Polymerization

      • Radical Polymerization

      • Anionic Polymerization

      • Cationic Polymerization

      • Copolymerization

    • Photochemistry of Bicyclobutane

  • Heterobicyclobutanes

  • Bicyclobuta-1(3)ene

    • Theoretical Background

    • Preparation and Mechanism

    • Synthetic Applications

  • Ionic Bicyclobutane

  • References