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
Copyright
Copyright 2013, all rights reserved. This open access ETD is published by Wright State University and OhioLINK.
