22. Aminocyclopropanes

  1. Zvi Rappoport
  1. E. Vilsmaier

Published Online: 28 JAN 2005

DOI: 10.1002/0470023449.ch22

Cyclopropyl Group: Volume 1 and Volume 2 (1987)

Cyclopropyl Group: Volume 1 and Volume 2 (1987)

How to Cite

Vilsmaier, E. (1987) Aminocyclopropanes, in Cyclopropyl Group: Volume 1 and Volume 2 (1987) (ed Z. Rappoport), John Wiley & Sons, Ltd, Chichester, UK. doi: 10.1002/0470023449.ch22

Editor Information

  1. The Hebrew University, Jerusalem, Israel

Author Information

  1. Fachbereich Chemie, Universität Kaiserslautern, D-6750 Kaiserslautern, West Germany

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



This chapter contains sections titled:

  • Introduction

  • Preparation

    • Introduction of an Amino Function into a Cyclopropane

      • Introduction by Cyclopropyl Migration

      • Introduction by Addition Reactions

        • Addition of Amines to Cyclopropanones

        • Addition of a Nitrogen Function to a Cyclopropene or a Methylene-cyclopropene

      • Introduction by Substitution Reactions

    • Cyclopropane Formation from a C(2) and a C(1) Unit

      • Cyclopropanation with Carbenes or Other Methylene Transfer Reagents

        • Simple Enamines or β-acceptor-substituted Enamines as C(2) Units

          • Heterosubstituted Carbenes as C(1) Unit

          • Simmons–Smith Reagent as C(1) Unit

          • Diazoalkanes as Carbene Precursors

          • Dimethylsulfoxonium Methylide as Methylene Transfer Reagent

        • Methylene Oxazolones, Thiazolones and Imidazolones as C(2) Units

        • Electron-deficient Double Bonds with a Nitrogen Function as C(2) Units

        • Normal Carbon-carbon Double Bonds as C(2) Units

      • Cyclopropanation with Dianion Precursors

        • Dianion Precursors and a C(2) Unit

        • Dianion Precursor and a C(1) Unit

      • Cyclopropanat Ion with Cyclopropenones and -thiones as C(1) Unit

    • Cyclopropane Formation by 1,3-ring-closure

      • Halogeno Enamines as Starting Materials

      • Enamino Sulfonium Salts as Starting Materials

      • Ring-contraction Reactions

      • Miscellaneous Starting Materials

    • Formation of Aminocyclopropanes by Photoreactions

      • Pyrrolinones as Starting Materials

      • Amino Ketones as Starting Materials

      • Amino-substituted Dienes as Starting Materials

      • Miscellaneous Starting Materials

    • Aminocyclopropanes from a Three-membered Ring Containing a Nitrogen Function

      • Nucleophilic Substitution at Aminocyclopropane Derivatives

      • Addition of Nucleophiles to Cyclopropaniminium Salts or Cyclopropanimine Isomers

      • Interconversion of the Nitrogen Functional Group

  • Reactions and Biochemical Activities

    • Reactions of Aminocyclopropanes

      • Reactions of the Amino Moiety

      • Nucleophilic Substitution Reactions

      • Ring-opening Reactions

        • Opening of the Vicinal Cyclopropane C(1)-C(2) Bond

        • Opening of the Distal Cyclopropane C(2)-C(3) Bond

        • Hydrogenolysis

        • Electrocyclic Ring-opening

      • Isomerization Reactions

      • Cyclopropane Cleavage by Cycloelimination

      • Removal of the Amino Function

        • By Formation of Cyclopropenes

        • Via Formation of a Methylenecyclopropane Intermediate

        • Via Formation of a Cyclopropanone

        • Via Formation of a Cyclopropyldiazonium, a Diazocyclopropane or a Cyclopropyldiazene Intermediate

    • Biochemical Activities and Applications of Aminocyclopropanes

      • 1-hydroxycyclopropylamines as Inhibitors of Acetaldehyde Dehydrogenase

      • Aminocyclopropanes with an Aryl or Heteroaryl Moiety as MAO Inhibitors

      • Aminocyclopropane Carboxylic Acid Derivatives

      • Aminocyclopropane Derivatives in Receptor Studies and Drug Design

      • The Aminocyclopropyl Group in Pesticides, Antiviral and Antibacterial Agents

      • The Aminocyclopropyl Group in Derivatives of Miscellaneous Activities

  • Acknowledgements

  • References