10. Organometallic Derivatives of Cyclopropanes and Their Reactions

  1. Zvi Rappoport Professor
  1. Zeev Goldschmidt

Published Online: 6 JUL 2004

DOI: 10.1002/0470023481.ch10

Cyclopropyl Group, Volume 2

Cyclopropyl Group, Volume 2

How to Cite

Goldschmidt, Z. (1995) Organometallic Derivatives of Cyclopropanes and Their Reactions, in Cyclopropyl Group, Volume 2 (ed Z. Rappoport), John Wiley & Sons, Ltd, Chichester, UK. doi: 10.1002/0470023481.ch10

Editor Information

  1. The Hebrew University, Jerusalem, Israel

Author Information

  1. Department of Chemistry, Bar–llan University, Ramat–Gan 52900, Israel

Publication History

  1. Published Online: 6 JUL 2004
  2. Published Print: 15 DEC 1995

Book Series:

  1. PATAI'S Chemistry of Functional Groups

Book Series Editors:

  1. Saul Patai and
  2. Zvi Rappoport

ISBN Information

Print ISBN: 9780471940746

Online ISBN: 9780470023488

SEARCH

Summary

This chapter contains sections titled:

  • Introduction

  • Metal Derivatives of Cyclopropane

    • Cyclopropyl–Metal Compounds

      • Direct Synthesis

      • Exchange Reactions

        • Metal–Halogen Exchange

        • Metathesis

        • Metallation

        • Metal Exchange

      • Addition

        • Cyclopropanation

        • Carbometallation

        • Oxidative Coupling

        • Oxymercuration

      • Insertion

        • Into a C[BOND]H Bond

        • Into a C[BOND]C Bond

      • Cyclization

      • Decarbonylation and Metal Migration

    • Cyclopropylcarbinyl–Metal Compounds

      • Main Group Elements

        • Reactions with Alkali Metals

        • Metal–halogen Exchange

        • Carbocyclization

        • Cyclopropanation

      • Transition Metal Complexes

        • Metal–Halogen Exchange

        • Hydrometallation

        • Carbocyclization

        • Insertion

        • Catalysis

    • Cyclopropylcarbene Complexes

      • Preparation

      • Reactions

        • without Ring Cleavage

        • Addition Reactions

        • Cycloadditions with Alkynes

        • Rearrangements

        • Reaction Intermediates

    • Cyclopropylcarbyne Complexes

      • Preparation

      • Reactions without Ring Cleavage

        • Ligand Substitution Reactions

        • Ring Substitution Reactions

        • Reactions with Phosphines

        • Reactions with Strong Acids

        • Photooxidation

      • Reactions Involving Ring Cleavage

        • Thermal Reactions in Chlorinated Solvents

        • Reactions with HCl

        • Reactions with Nucleophiles

        • Photooxygenation in Chlorinated Solvents

    • Vinylcyclopropane–Metal Derivatives

      • Main Group Elements

        • Exchange Reactions

        • Carbometallations

        • Rearrangements

      • Transition Metal Complexes

        • σ-bonded Complexes

        • π-complexes of Vinylcyclopropanes

      • Conjugated Vinylcyclopropane Complexes

        • Acyclic η4-dienyl Complexes

        • Cyclic Complexes

    • Alkynylcyclopropane–Metal Derivatives

      • Cyclopropylethynyl–metal Derivatives

      • 1-Alkynylcyclopropyllithium

      • Dimetallation

      • Reduction Reactions

      • Hydration

      • η1-transition Metal Complexes

      • Reactions Involving Metal π-bonding

      • Cyclopropylalkynylcarbene Complexes

  • Cyclopropylidene Complexes

    • Tungsten Complexes

    • Iron Complexes

      • μ-cyclopropylidene Complexes

      • Cyclopropenylium Complexes

  • Metal Derivatives of Cyclopropene

    • σ-bonded Compounds

      • 1-cyclopropenylmetal Compounds

        • Main Group Elements

        • Transition Metal Complexes

      • 3-cyclopropenylmetal Compounds

        • Preparation

        • Reactions

    • π-complexes

      • Synthesis and Characterization

        • Ligand Exchange

        • Coupling of Alkynes with Alkylidene Complexes

        • β-hydride Elimination

      • Reactions

        • Isomerization to Vinyl Carbene Complexes

        • Rearrangement to Metallacyclobutenes

        • Reaction with Alkynes and Alkenes

        • Oxidative Coupling Reactions

  • η3-cyclopropenyl Complexes (Metallatetrahedranes)

    • Preparation

      • Oxidative Addition of Cyclopropenylium Salts

      • Metallacyclobutadiene Rearrangements

      • Reaction of Carbyne Complexes with Alkynes

    • Reactions

      • Ligand Exchange

        • Exchange of CO by Phosphorus, Nitrogen and Oxygen Ligands

        • Exchange of CO by Alkenes and Alkynes

        • Exchange of Ligands by Cyclopentadienyl and Related Groups

        • Metathetical Exchanges of Halogen and Nitrogen Ligands

      • Ring Enlargement Reactions

      • Addition Reactions

    • Structural Aspects

      • Solid State Structure

      • Electronic Structure

      • Dynamic Behavior

  • Cyclopropenylidene Complexes

    • Cyclopropenylidene Complexes

      • Preparation

        • From 3,3-dichlorocyclopropenes

        • From Halocyclopropenylium Salts

        • From Alkoxycyclopropenylium Salts

        • From Lithiocyclopropenylium Salts

        • By Desulfurization and Deselenization

    • Metallacyclopropenylium Compounds

      • Preparation

        • Main Group Metal Compounds

        • Transition Metal Complexes

      • Reactions

      • NMR Spectra

  • Metal Derivatives of Methylenecyclopropane

    • σ-bonded Compounds

      • Metallation

      • Metal–Halogen Exchange

      • Reactions with Metals

    • π-complexes

      • Preparation

        • Ligand Exchange Reactions

        • Cyclopropanation of Allenes

      • NMR Spectra

      • Reactions

        • Chloropalladation

        • Hydroplatination

        • Reactions of η2-methylenecyclopropane Complexes

        • η4-trimethylenemethane Complexes

        • The Pauson–Khand Reaction

      • Catalyzed Cycloaddition Reactions

        • Intermolecular Cycloadditions

        • Intramolecular Cycloadditions

  • Methylenecyclopropene Complexes (Triafulvenes)

  • Acknowledgments

  • References