Piatak, David M.
M.S. (Master of Science)
Department of Chemistry
Amides; Cyclic compounds; Organic electrochemistry; Oxidation; Electrolytic
The electrooxidation of N-chlorobenzoyl(o, m & p) , p- nitrobenzoyl and pivaloic acid amides of pyrroldine, piperidine and morpholine was carried out using a double mediatory acetonitrile-water system containing ruthenium tetraoxide and CIO-. This clean and facile method afforded the corresponding imides in good yields. The p- chlorobenzoyl amide of pyrrolidine and piperidine reacted better than the ortho and meta analogues and the p- nitrobenzoyl isomer. After Ru04 oxidation, the pivaloic acid amide of piperidine hydrolysed to an open chain acid amide product 7a. Complex intractable mixtures were obtained in the corresponding oxidation of morpholine amides, with the exception of o-chlorobenzoyl amide 3d, which yielded its corresponding imide 6d.
Subramanian, Sharadha, "Ruthenium tetraoxide catalyzed electrooxidation of cyclic amides" (1994). Graduate Research Theses & Dissertations. 4798.
Northern Illinois University
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