Date of Submission

Spring 2023

Academic Program

Chemistry and Biochemistry

Project Advisor 1

Emily McLaughlin

Abstract/Artist's Statement

Carbon-nitrogen (C-N) bonds are ever-present in both natural and unnatural small molecules, especially those with potential bioactivity. Previously, the research done has been centered in developing new synthetic methods to create two C-N bonds, simultaneously, to afford substituted aziridine products. This work is focused on the design of a visible light-driven process where a metal photocatalyst alongside blue LED light promotes the direct aziridination of substituted alkenes (C=C) using N-aminopyridinium ylides as the nitrogen source. Reports in the literature have recently proven that nitrenes can be generated from azidoformates using visible light catalysis and will form aziridines in the presence of olefins. Furthermore, previous experiments have successfully identified N-aminopyridinium (1) as an effective nitrogen source for our aziridination trials. Upon these findings the focus of this research has turned towards understanding more about the mechanism of the aziridination reaction. We report our investigation on the presence of a singlet or triplet nitrene, which has a direct effect on the potential stereochemistry selectivity on this reaction.

Open Access Agreement

On-Campus only

Creative Commons License

Creative Commons License
This work is licensed under a Creative Commons Attribution-Noncommercial-No Derivative Works 4.0 License.

This work is protected by a Creative Commons license. Any use not permitted under that license is prohibited.

Bard Off-campus Download

Bard 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.