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Base Promoted 5-endo-dig Cyclizations of Non-Conia-ene Propargyl Ethers: A Mechanistic Investigation
| Title: | Base Promoted 5-endo-dig Cyclizations of Non-Conia-ene Propargyl Ethers: A Mechanistic Investigation. |
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| Name(s): |
Hintze, Silas Q. , author Lepore, Salvatore D. , Thesis advisor Florida Atlantic University, Degree grantor Department of Chemistry and Biochemistry Charles E. Schmidt College of Science |
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| Type of Resource: | text | |
| Genre: | Electronic Thesis Or Dissertation | |
| Date Created: | 2024 | |
| Date Issued: | 2024 | |
| Publisher: | Florida Atlantic University | |
| Place of Publication: | Boca Raton, Fla. | |
| Physical Form: | application/pdf | |
| Extent: | 110 p. | |
| Language(s): | English | |
| Abstract/Description: | Herein, we discuss a novel method for the synthesis of decorated 2,5-dihydrofurans. The base promoted 5-endo-dig cyclization of non-Conia-ene propargyl ethers produces 2,2 disubstituted dihydrofurans. Central to the reaction is the presence of an acidic C–H bond which is activated by an adjacent aromatic heterocycle. The transformation is viable with a wide range of substituents, including N, O, and S containing heterocycles, substituted phenyl rings, and alkyl groups. The cyclization proceeds within 30 seconds at room temperature under the action of potassium tert-butoxide. This work stands apart from the current literature due to the absence of transition metal catalysts and/or harsh reaction conditions. A thorough mechanistic investigation is undertaken to better understand the nature of this unprecedented reaction. | |
| Identifier: | FA00014376 (IID) | |
| Degree granted: | Thesis (MS)--Florida Atlantic University, 2024. | |
| Collection: | FAU Electronic Theses and Dissertations Collection | |
| Note(s): | Includes bibliography. | |
| Subject(s): |
Cyclization (Chemistry) Chemistry, Organic |
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| Persistent Link to This Record: | http://purl.flvc.org/fau/fd/FA00014376 | |
| Use and Reproduction: | Copyright © is held by the author with permission granted to Florida Atlantic University to digitize, archive and distribute this item for non-profit research and educational purposes. Any reuse of this item in excess of fair use or other copyright exemptions requires permission of the copyright holder. | |
| Use and Reproduction: | http://rightsstatements.org/vocab/InC/1.0/ | |
| Host Institution: | FAU |
