This grant from the Organic Dynamics Program supports the research of Professor Baumstark at Georgia State University. The results of this research will give new understanding to the mechanism of oxygen atom transfer from dioxiranes and from activated hydroperoxides. This type of oxidation reaction is important in the synthesis of organic compounds and it is a common type of reaction in biological systems. The possibility of light-producing chemical reactions will also be explored. Oxygen transfer reactions will be explored with dioxiranes (three- membered ring peroxides) and activated hydroperoxides. The use of oxygen-17 labeling will play a key role in mechanistic and structural studies. Substrates for oxidation studies with dioxirane are: saturated hydrocarbons, alkenes, and polycyclic aromatic compounds. The synthesis and reactions of a series of activated hydroperoxides will be investigated. These compounds have the common structural feature of an alpha-azohydroperoxy group. In addition, these hydroperoxides may provide insight to biological oxidations which involve the flavin 4a-hydroperoxide.
