Chapter 19. Mechanisms of Enamine Hydrolysis

  1. Zvi Rappoport Professor
  1. James R. Keeffe1 and
  2. A. Jerry Kresge2

Published Online: 20 JUL 2004

DOI: 10.1002/0470024763.ch19

Enamines (1994)

Enamines (1994)

How to Cite

Keeffe, J. R. and Kresge, A. J. (1994) Mechanisms of Enamine Hydrolysis, in Enamines (1994) (ed Z. Rappoport), John Wiley & Sons, Ltd, Chichester, UK. doi: 10.1002/0470024763.ch19

Editor Information

  1. The Hebrew University, Jerusalem, Israel

Author Information

  1. 1

    Department of Chemistry and Biochemistry, San Francisco State University, San Francisco, California 94132, USA

  2. 2

    Department of Chemistry, University of Toronto, Toronto, Ontario M5S 1A1, Canada

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

SEARCH

Summary

This chapter contains sections titled:

  • Introduction

  • Protonation of Enamines

    • Equilibrium Basicity

      • General Features

      • Effects of Amino Group Structure on Basicity

      • Effects of Alkene Group Structure on Basicity

      • Gas-phase Basicity of Enamines

  • Hydrolysis Mechanisms

    • N-alkylenamines of Isobutyraldehyde

      • The Higher pH Region

      • The Middle pH Region

      • The Lower pH and Ho Region

    • N-alkylenamines of Propiophenone

      • The Higher pH Region

      • The Middle pH Region

      • The Lower pH and Ho Region

    • β-cyanoenamines

    • β-carboethoxyenamines

    • N-arylenamines of Isobutyraldehyde, Cyclohexanone and 2-methylcyclohexanone

    • Miscellaneous Enamines and Some Related Compounds

      • Two β-arylenamines

      • Some Enaminones

      • Two 1,4-dihydropyridines

      • Modified Enamines: Aminoarenes, Enamides and Pyrroles

    • A Brief Summary of Section III

  • Comparisons Among Nucleophilic Alkenes

    • Equilibrium Basicities of X[BOND]C[DOUBLE BOND]C Compounds

    • Kinetic Basicities of X[BOND]C[DOUBLE BOND]C Compounds

    • Enamine vs Enol Pathways in Amine-catalyzed Reactions

  • References and Notes