Sign In

19.22 : Amines to Alkenes: Cope Elimination

Cope elimination reaction involves the conversion of tertiary amines to alkene using hydrogen peroxide under thermal conditions, as depicted in figure 1.

Figure1

Figure 1. The Cope elimination reaction

The mechanism of the reaction is illustrated in Figure 2. Here, the oxidation of tertiary amines by hydrogen peroxide yields amine oxide. Subsequently, the thermally induced elimination of the N,N-dimethyl hydroxylamine as leaving group occurs. However, it produces a less substituted alkene as the major product. In this process, amine oxide, in the role of a base, follows the syn stereochemistry and proceeds through a cyclic transition state.

Figure2

Figure 2. The mechanism of the Cope elimination reaction

Cope elimination is helpful for the synthesis of reactive/sensitive alkenes because the reaction occurs under mild conditions.

Tags
Cope EliminationTertiary AminesAlkenesHydrogen PeroxideThermal ConditionsAmine OxideNN dimethyl HydroxylamineSyn StereochemistryCyclic Transition StateAlkene SynthesisMild Conditions

From Chapter 19:

article

Now Playing

19.22 : Amines to Alkenes: Cope Elimination

Amines

1.8K Views

article

19.1 : Amines: Introduction

Amines

3.8K Views

article

19.2 : Nomenclature of Primary Amines

Amines

3.0K Views

article

19.3 : Nomenclature of Secondary and Tertiary Amines

Amines

3.2K Views

article

19.4 : Nomenclature of Aryl and Heterocyclic Amines

Amines

2.0K Views

article

19.5 : Structure of Amines

Amines

2.2K Views

article

19.6 : Physical Properties of Amines

Amines

2.6K Views

article

19.7 : Basicity of Aliphatic Amines

Amines

5.3K Views

article

19.8 : Basicity of Aromatic Amines

Amines

6.6K Views

article

19.9 : Basicity of Heterocyclic Aromatic Amines

Amines

4.9K Views

article

19.10 : NMR Spectroscopy Of Amines

Amines

7.4K Views

article

19.11 : Mass Spectrometry of Amines

Amines

3.8K Views

article

19.12 : Preparation of Amines: Alkylation of Ammonia and Amines

Amines

2.9K Views

article

19.13 : Preparation of 1° Amines: Azide Synthesis

Amines

3.6K Views

article

19.14 : Preparation of 1° Amines: Gabriel Synthesis

Amines

3.2K Views

See More

JoVE Logo

Privacy

Terms of Use

Policies

Research

Education

ABOUT JoVE

Copyright © 2025 MyJoVE Corporation. All rights reserved