With this new award the Organic and Macromolecular Chemistry Program supports the work of Dr. JoAnn P. DeLuca at Central Washington University in Ellensburg, Washington. The research aims to investigate the use of ylides as precursors for the pyrolytic or photolytic generation of carbene intermediates, and their capture by substrates to form stable organic products. A series of ylides will be examined, encompassing a wide range of stabilities, looking for correlations between the ability of the ylide to act as a precursor and its calculated carbene-nucleophile bond energy.
Carbenes - carbon species like R2C: in which R is a carbon or hydrogen and the carbon has a pair of nonbonding electrons - are useful intermediates for the formation of a variety of organic compounds. They have usually been generated by heating or uv radiation of diazoalkanes or diazirenes, compounds that can be thought of as adducts of a carbene with N2. This project will study ylides, compounds where carbenes are combined with other two-electron donors, such as pyridine, in search of better precursors for organic synthesis. The work will include precursor synthesis, mechanism studies, and theoretical computations, and provide excellent training for the undergraduate and masters degree students involved. The PI is playing a leadership role in involving these students in research and nurturing their interest in going on to advanced degrees.
