Publication Date

2013

Document Type

Thesis

Committee Members

William Feld (Advisor), David Grossie (Committee Member), Kenneth Turnbull (Committee Member)

Degree Name

Master of Science (MS)

Abstract

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.

Page Count

99

Department or Program

Department of Chemistry

Year Degree Awarded

2013


Included in

Chemistry Commons

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