Reactions of singlet oxygen with sulfides, sulfenates, allyl stannanes, and organotellurium compounds will be studied. The results of this research will be three-fold: 1) An expanded mechanistic understanding of oxidation reactions; 2) The development and utilization novel oxidizing agents; and 3) Oxidation of novel substrates that will provide new synthetic methods for the formation of potentially useful materials. In the course of this investigation, the effects of neighboring groups on sulfide photooxidations will be studied, the synthesis and properties of persulfenic acids and hydroperoxy sufuranes will be examined, and the ability of these new classes of oxidizing agents to transfer oxygen to heteroatoms and unsaturated substrates will be studied. %%% This grant from the Organic Dynamics Program supports the continuing work of Professor Edward Clennan at the University of Wyoming. Molecular oxygen can be exposed to high intensity light in the presence of a dye to generate an excited state of oxygen, which is referred to as singlet oxygen. This excited state species is a short-lived reactive molecule, which will oxidize various organic molecules. In this project, the detailed steps in the reaction of singlet oxygen with organic molecules will be studied. Furthermore, the reactive intermediates that are generated in certain of these oxidations will be used to transfer oxygen atoms to other organic molecules in a specific manner. This has potential application in the synthesis of unique molecules.
