Synthesis and Study of Carbene Intermediates

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Authors
Dailey, Tyler
Lohar, Noah
Advisor
Rowley, John
Pharr, Caroline
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Date of Issue
2024
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Title
Synthesis and Study of Carbene Intermediates
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Abstract
Carbene intermediates are of interest due to their high reactivity, use in carbon-carbon bond-forming reactions, and prevalence in interstellar space. Carbene species are found in comets, atmospheres of carbon stars, and have also been identified in cool molecular gas clouds. Further information about carbene intermediates could inform us about ion-molecular interactions and provide insight into the origin of the universe and its destiny. Applications of carbene intermediates include their use in the synthesis of pharmaceuticals, plastics, and polymers used daily by consumers. This study focuses on the synthesis of sulfonium ylide precursor molecules to malonate and beta-diketone carbene intermediates of interest. Varied steric and electronic properties resulting from different substituents on the derivatives will allow for the investigation of carbene abundance and spin state distribution. The proposed synthetic pathway includes a two-step synthesis proceeding through a diazo precursor molecule, which will then be used to form the sulfonium ylide. Upon successful synthesis of the sulfonium ylide derivatives, trapping experiments will be performed via photolysis to study the carbene intermediates of interest.
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Chemistry