William Feld (Advisor), David Grossie (Committee Member), Kenneth Turnbull (Committee Member)
Master of Science (MS)
An SN2 reaction between 1,3-dichloroacetone and benzenesulfinic acid sodium salt was carried out to produce 1,3-bis(phenylsulfonyl)acetone. A crystal structure for 1,3-bis(phenylsulfonyl)acetone was obtained. The SN2 reaction was followed by a condensation reaction with benzil but this did not yield a condensation product. A photo-active compound, 2,5-dicarboethoxy-3,4-di(4-methylphenyl)cyclopentadienone, was synthesized and was shown to undergo a unique, solid-state dimerization. Several reactions involving the ester functions were carried out but these did not yield the expected products, instead, structural rearrangements seemed to predominate. An asymmetric cyclopentadienone, 2-carbomethoxy-5-methyl-3,4-diphenylcyclopentadienone, was synthesized and it was reacted with norbornadiene to produce methyl 4-methyl-2,3-diphenylbenzoate. The benzoate was reduced to 4-methyl-2,3-diphenylbenzyl alcohol that was either converted to 4-methyl-2,3-diphenylbenzyl chloride with thionyl chloride or oxidized with manganese dioxide to 4-methyl-2,3-diphenylbenzaldehyde. The benzaldehyde derivative was reacted with a phenylated bisphosphonium salt to produce an oligomeric PPV derivative, 1,4-bis(2,3-diphenyl-4-methylphenyl)ethenyl-2,3-diphenylbenzene.
Department or Program
Department of Chemistry
Year Degree Awarded
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