Date of Submission
Spring 2015
Academic Programs and Concentrations
Chemistry
Project Advisor 1
Emily McLaughlin
Abstract/Artist's Statement
Catalytic, intramolecular aziridination of alkenes continues to be a popular methodology for the preparation of amine-derived heterocycles. Various transition-metal complexes, especially dirhodium complexes, have been reported for their catalytic activities in these reactions. Recent work has shown that metal-catalyzed intramolecular addition of nitrogen to alkenes can be achieved both inter- and intramolecularly with sulfonamides and carbamates. Our research utilizes phenyl and benzyl carbamates as starting compounds for an optimized intramolecular N-insertion onto pendant alkenes. These reactions are designed to access benzoxazepine and benzoxazinone molecular scaffolds. We report our recent observations in the synthesis of these aziridines and resultant nucleophilic attack/ring opening. Reaction optimization, mechanistic insights, and the scope and limitations of our methodology are discussed.
Open Access Agreement
On-Campus only
Creative Commons License
This work is licensed under a Creative Commons Attribution-Noncommercial-No Derivative Works 3.0 License.
Recommended Citation
Atuk, Emin Berk, "Metal Catalyzed, Microwave-Mediated, Intramolecular Aziridination: Synthesis of Benzoxazepine and Benzoxazinone Derivatives" (2015). Senior Projects Spring 2015. 181.
https://digitalcommons.bard.edu/senproj_s2015/181
This work is protected by a Creative Commons license. Any use not permitted under that license is prohibited.
Bard Off-campus DownloadBard College faculty, staff, and students can login from off-campus by clicking on the Off-campus Download button and entering their Bard username and password.