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A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species
Published on: August 16, 2018
Cycloaromatization protocol for synthesis of polysubstituted phenol derivatives: method development and mechanistic
William T Spencer1, Alison J Frontier
1Department of Chemistry, University of Rochester, Rochester, New York 14627, USA.
The Journal of Organic Chemistry
|August 16, 2012
Summary
This study explores the cycloaromatization of propargylic ethers, yielding highly substituted phenol derivatives under simple, air-insensitive conditions. The reaction mechanism involves electrocyclization and proton transfer.
Area of Science:
- Organic Chemistry
- Synthetic Chemistry
Background:
- Propargylic ethers are versatile organic compounds.
- Cycloaromatization reactions are important for synthesizing cyclic structures.
Purpose of the Study:
- To explore the scope of cycloaromatization of propargylic ethers.
- To develop operationally simple and air- and moisture-insensitive reaction conditions.
Main Methods:
- Reaction of propargylic ethers under specific conditions.
- Exploration of substrate scope.
- Mechanistic studies including electrocyclization and proton transfer investigation.
Main Results:
- Highly substituted phenol derivatives were synthesized.
- High yields of the desired products were achieved.
- Reaction conditions were found to be simple, air- and moisture-insensitive.
Conclusions:
- The cycloaromatization of propargylic ethers is an efficient method for phenol derivative synthesis.
- The reaction proceeds via a proposed electrocyclization followed by 1,3-proton transfer mechanism.
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