Reactivity of the vinylogous epoxyketone moiety with stabilized B-dicarbonyl enolate anions
Date of Graduation
Master of Science in Chemistry
The lipid peroxidation process produces lipid hydroperoxides which decompose to a variety of secondary lipid peroxidation products such as epoxides, aldehydes, and ketones. A vinylogous epoxyketone, (E)-5,6-epoxy-3-nonen-2-one was chosen as a model of one lipid oxidation product. The synthesis and characterization of the model are presented. The reaction of the enolate of diethyl malonte with the model compound produces a lactone functional group. The reactions of the enolates of ethyl acetoacetate and 2,4-pantanedione do not produce a lactone but give novel products. The spectroscopic analysis of these products will be presented. The reactivity of enolates with the model compound is presented along with an explanation of reactivity differences.
© Jie Zhang
Zhang, Jie, "Reactivity of the vinylogous epoxyketone moiety with stabilized B-dicarbonyl enolate anions" (1997). MSU Graduate Theses. 2882.