CAREER: Synthetic methodology for the preparation of polycyclic nitrogen or oxygen containing heterocycles

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With this CAREER Award, the Organic and Macromolecular Chemistry Program is supporting the research of Professor Matthias Brewer of the Chemistry Department at the University of Vermont. This project will develop new methods for the synthesis of nitrogen or oxygen containing organic compounds from simple starting materials. These methods, based on the reaction of hydrazones with sulfonium ions, will provide new ways to access reactive intermediates under mild and environmentally benign conditions. These reactive intermediates will be studied for their ability to participate in unprecedented sigmatropic rearrangements, electrophilic aromatic substitutions, and cycloadditions, and will also be evaluated for reactivity in a variety of synthetic transformations. This research will provide biomedical researchers with new tools to prepare biologically active compounds that are often difficult to synthesize by current methods.Professor Brewer will also initiate educational projects focused on the development of environmentally beneficial green chemical methods and their integration into the undergraduate curriculum. Green chemistry experiments will be developed in senior-level organic laboratories for use in the lower-level undergraduate laboratories. The PI will also oversee a partnership between undergraduate students and a local aquarium/science center to develop outreach educational materials designed to introduce a general audience to environmentally benign green chemistry.