M.S. (Master of Science)
Department of Chemistry
Organonitrogen compounds; Cerium; Erythrina stricta; Bark--Analysis; Oxidation
Ceric ammonium nitrate is a mild but multi-functional oxidizing agent for many organics. In this work, the oxidation of 1,17- diacetoxy-4-methylestra-l,3,5(10)triene by cerium(IV) was studied. The desired result was the incorporation of the nitrato moiety at the 4-methyl position. This incorporation could then be utilized to eliminate the carbon atom attached to C-4 to yield 1-oxygenated estrogens. The results of varying reaction parameters in this reaction were largely negative, but yielded much information; the yield, however, did not exceed 20 mole per cent. The most important conclusion that can be drawn from this work is that the incorporation of the nitrato group at the benzylic methyl position does not involve a carbonium ion intermediate. The reaction mechanism is more likely the formation of an alkyl-Ce(IV) intermediate which goes to product either through oxidative displacement or a ligand transfer mechanism. The chemical constitution of certain species of the genus Erythrina is fairly well known. The GLC analyses of Erythrina stricta bark extract fractions has been performed in this work.
Nowicki, Wayne A., "Cerium(IV) oxidation of 1,17-diacetoxy-4-methylestra-1,3,5(10)-triene and GLC analysis of Erythrina stricta" (1980). Graduate Research Theses & Dissertations. 1706.
v, 35 pages
Northern Illinois University
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