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Ethylene-promoted intermolecular enyne metathesis
Anthony J Giessert1, Nicholas J Brazis, Steven T Diver
1Department of Chemistry, University at Buffalo, the State University of New York, Amherst, New York 14260, USA.
Organic Letters
|October 11, 2003
Summary
Ethylene cometathesis enables intermolecular enyne metathesis with functionalized molecules. Optimizing ethylene concentration prevents side reactions and enhances reaction rates, showcasing its dual role.
Area of Science:
- Organic Chemistry
- Catalysis
- Polymer Science
Background:
- Enyne metathesis is a powerful carbon-carbon bond-forming reaction.
- Functional group-rich substrates present challenges in metathesis reactions.
- Ethylene metathesis is a known process that can compete with other metathesis reactions.
Purpose of the Study:
- To investigate the use of ethylene cometathesis to promote intermolecular enyne metathesis.
- To optimize ethylene concentration for efficient enyne metathesis.
- To understand the role of ethylene in the reaction mechanism.
Main Methods:
- Intermolecular enyne metathesis reactions were performed using functional group-rich alkynes and vinyl ethers.
- Ethylene gas was introduced as a cometathesis partner.
- Ethylene concentration was systematically varied and optimized.
Main Results:
- Ethylene cometathesis successfully promoted intermolecular enyne metathesis between complex substrates.
- Optimized ethylene concentration minimized the formation of butadiene from background ethylene metathesis.
- Ethylene was found to play a dual role, acting as both a protective agent and a rate enhancer.
Conclusions:
- Ethylene cometathesis is an effective strategy for enabling challenging intermolecular enyne metathesis reactions.
- Careful control of ethylene concentration is crucial for maximizing yield and minimizing side products.
- The findings provide valuable insights into the mechanism and application of ethylene-promoted metathesis.