Anodic Oxidations and Their Applications to Organic Synthesis

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This research involves several areas of study using anodic oxidation for the preparation of novel compounds, or compounds difficultly available via conventional chemistry. First, the anodic oxidation of p-hydrogen and p-alkyl anilides will be studied as a route to acylated quinone imine ketal and quinol ethers. These compounds, which are not available from conventional routes, can serve as key intermediates in organic synthesis. The second area, and major emphasis of the work, is development of high-yield anodic carbon-carbon bond-forming reactions. The initial studies will be directed at intramolecular trapping of oxidized phenol intermediates with unsaturated linkages resulting in carbon-carbon bond formation. The products obtained from 4-(2'-unsaturated-aryl)-phenols are 2,5-cyclohexadienones which are important intermediates in organic synthesis. The objectives are to understand how substituents on both the aryl and phenol rings influence the yield of the anodic carbon-carbon bond-forming reaction and utilize this knowledge for the efficient preparation of useful compounds or intermediates. Another objective is to investigate the use of the products obtained from these anodic oxidation studies in organic synthesis. %%% With this award the Synthetic Organic Program of the Chemistry Division will support the research of Dr. John S. Swenton of the Department of Chemistry at Ohio State University. The research involves the study of anodic oxidation chemistry for the preparation of novel compounds, or compounds difficultly available via conventional chemistry. This approach using synthetic electrochemistry is very timely since it serves as a reagentless method for effecting oxidations, reductions, and carbon-carbon bond formation. With the proper selection of electrode and experimental conditions, electrochemistry is the environmental choice for conducting chemical transformations since there is no spent oxidant or reductant to be disposed of or recycled after the reaction.