22.7 Cope Elimination
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- 22.1 Classification of Amines
- 22.2 Nomenclature of Amines
- 22.3 Basicity of Amines
- 22.4a Synthesis of Amines Reduction
- 22.4b Synthesis of Amines Hofmann Rearrangement
- 22.4c Synthesis of Amines Curtius Rearrangement and Schmidt Reaction
- 22.4d Synthesis of Amines Gabriel Synthesis
- 22.4e Synthesis of Amines Reductive Amination
- 22.5 Acylation
- 22.6 Hofmann Elimination
- 22.7 Cope Elimination
- 22.8a Reaction with Nitrous Acid and the Sandmeyer Reactions
- 22.8b Azo Coupling
- 22.9 EAS Reactions with Nitrogen Heterocycles
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Cope Elimination
The Cope Elimination is an elimination reaction specifically for tertiary amines for which the major organic product is an alkene. The leaving group involved (a hydroxyl amine) is a moderate base and therefore is not a good leaving group. As a result, the major product is the Hofmann product (a.k.a. anti-Zaitsev product--the least substituted alkene). An explanation for why a poor leaving group results in the Hofmann product can be found here: 7.7b Exceptions to Zaitsev’s Rule for E2 Reactions.
Cope Elimination Mechanism
The Cope Elimination occurs over the course of two steps:
- Step 1 - Oxidation -- The oxidation of a tertiary amine to an amine oxide using hydrogen peroxide.
- Step 2 Elimination - The amine oxide produced in step 1 undergoes E2 elimination. This step is unique in that the oxide portion of the leaving group serves as the base involved in the elimination reaction.
