Date of Submission
Chemistry and Biochemistry
Project Advisor 1
Our goal in this project is to form cyclobutane rings. While normally this is done using UV light, we have chosen to explore an alternative method, that being visible light based [2 + 2] cycloaddition, in the hopes of better understanding its limits and mechanism. Excitation of organic molecules by UV light is able to form radicals, meaning it is efficient, but apart from that efficiency, it comes with several problems. It’s expensive, potentially hazardous, and its reactivity is hard to control, leading to undesired products forming. Visible light based reactions lack these disadvantages, but can be unable to form product without the presence of a catalyst. In the effort to better understand this process, we have used it to form cyclobutanes out of an alkene, and a vinylogous ester. We are interested in how it interacts with vinylogous esters as they possess both electron rich and electron deficient regions. As this field is new, the mechanism by which this reaction proceeds is not well-understood. We seek to elucidate the mechanism of this reaction by looking into the resulting regiochemistry of the product.
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This work is licensed under a Creative Commons Attribution-Noncommercial-No Derivative Works 4.0 License.
Pichkhadze, Nye A., "Regioselectivity of the [2 + 2] Cycloaddition of Vinylogous Esters using Visible Light Photocatalysis" (2023). Senior Projects Spring 2023. 26.
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