Anodic Oxidations and Their Applications to Organic Synthesis

这项研究涉及几个领域的研究，使用阳极 用于制备新化合物或化合物的氧化方法 难以通过常规化学方法获得。一是 p-氢和p-烷基苯胺的阳极氧化将 作为酰化醌亚胺缩酮和醌醇的路线进行研究 乙醚这些化合物不能从 传统的路线，可以作为关键的中间体，在有机 合成.第二个范畴，也是这项工作的重点，是 碳-碳键形成的高产量阳极的发展 反应.初步研究将针对 氧化苯酚中间体的分子内捕获 导致碳-碳键形成的不饱和键。 由4-（2 '-不饱和-芳基）-苯酚得到的产物是 2，5-环己二烯酮，其是制备抗氧化剂的重要中间体， 有机合成目标是了解 芳基环和酚环上的取代基影响 阳极碳-碳键形成反应的产率， 利用这些知识有效地制备有用的 化合物或中间体。另一个目标是调查 由这些阳极氧化获得的产物的用途 研究有机合成。 %%% 凭借这一奖项，化学合成有机计划 该司将支持约翰·S.斯旺顿， 俄亥俄州州立大学化学系。的 研究涉及阳极氧化化学的研究， 新化合物或难以制备的化合物的制备 可通过常规化学方法获得。这种方法使用 合成电化学是非常及时的，因为它作为一个 用于实现氧化、还原和 碳-碳键形成。通过适当选择 电极和实验条件，电化学是 进行化学转化的环境选择 由于没有待处理的废氧化剂或还原剂 或在反应后再循环。

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.