Chapter 22. 1, 1-Enediamines

  1. Zvi Rappoport Professor
  1. Zhi-Tang Huang and
  2. Mei-Xiang Wang

Published Online: 20 JUL 2004

DOI: 10.1002/0470024763.ch22

Enamines (1994)

Enamines (1994)

How to Cite

Huang, Z.-T. and Wang, M.-X. (1994) 1, 1-Enediamines, in Enamines (1994) (ed Z. Rappoport), John Wiley & Sons, Ltd, Chichester, UK. doi: 10.1002/0470024763.ch22

Editor Information

  1. The Hebrew University, Jerusalem, Israel

Author Information

  1. Institute of Chemistry, Academia Sinica, Beijing 100080, People's Republic of China

Publication History

  1. Published Online: 20 JUL 2004
  2. Published Print: 31 AUG 1994

Book Series:

  1. PATAI'S Chemistry of Functional Groups

Book Series Editors:

  1. Saul Patai and
  2. Zvi Rappoport

Series Editor Information

  1. The Hebrew University, Jerusalem, Israel

ISBN Information

Print ISBN: 9780471933397

Online ISBN: 9780470024768

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Summary

This chapter contains sections titled:

  • Introduction

  • Structure and Physical Properties

    • Structure and Reactivity

    • Spectroscopic Data

  • Preparation of 1,1-enediamines

    • Reaction of Amines with Ketene Dithioacetals

    • Reaction of Amines with Ketene Acetals and gem-Dihaloethylenes

    • Reaction of Amines with Ketene N,S-, or N,O-acetals and α-haloenamines

    • Reaction of Aliphatic Amides with Tetrakis(dimethylamino)titanium

    • Reaction of Active Methyl and Methylene Compounds with Urea Acetals, S-alkylated Thioureas and Carbodiimides

    • Acylation of 1-alkyl-2-methylamidine Derivatives

    • Miscellaneous Preparative Methods

  • 1,1-enediamines as Nucleophiles in Substitution and Addition Reactions

    • Protonation

    • Alkylation and Arylation

      • With Alkyl Halides

      • With Acetylenes

      • With Electrophilic Olefins

      • Arylation

      • With Aldehydes and Ketones

    • Acylation

      • With Carboxylic Acid Halides and Ketenes

      • With Isocyanates and Isothiocyanates

    • Reaction with Other Electrophiles

      • With Azodicarboxylate Esters

      • Halogenation

      • Miscellaneous Reactions

  • Cycloaddition Reactions of 1,1-enediamines

    • 1,2-cycloaddition

    • 1,4-cycloaddition

    • 1,3-dipolar Cycloaddition

  • Miscellaneous Reactions

  • References