Publication Date
1999
Document Type
Thesis
Committee Members
William Feld (Advisor)
Degree Name
Master of Science (MS)
Abstract
The reaction of diethyl 2,5-dihydroxyterephthalate with allyl bromide/K2CO3 in DMF followed by hydrolysis provided 2,5-di(allyloxy)terephthalic acid. The conversion of 2,5-di (allyloxy)terephthalic acid to 1,4-di(2-benzoxazolyl)-2,5-di(allyloxy)benzene in PPSE was unsuccessful. However, the reaction of 1,4-di(2-benzoxazolyl)-2,5- dihydroxybenzene with allyl bromide/K2CO3 provided 1,4-di(2-benzoxazolyl)-2,5- di(allyloxy)benzene. DSC analysis indicated that 1,4-di(2-benzoxazolyl)-2,5- di(allyloxy)benzene undergoes a Claisen rearrangement to the corresponding diallyl product. The synthesis of 2-allyloxy-1,4-di(2-benzoxazolyl)benzene was carried out using 2-hydroxy-1,4-di(2-benzoxazolyl)benzene as starting material. DSC analysis was inconclusive with respect to a Claisen rearrangement. The reaction of 2-allyloxybenzoic acid with 2,2-bis(3-amino-4-hydroxyphenyl)-1,1,1,3,3,3-hexafluoropropane in PPSE was unsuccessful but the reaction of 2,2-bis(2-(2-hydroxyphenyl)-5-benzoxazolyl)-1,1,1,3,3,3-hexafluoropropane with allyl bromide/K2CO3 in DMF provided 2,2-bis(2-(2- allyloxyphenyl)-5-benzoxazolyl)-1,1,1,3,3,3-hexafluoropropane. DSC analysis of 2,2- bis(2-(2-allyloxyphenyl)-5-benzoxazolyl)-1,1,1,3,3,3-hexafluoropropane was inconclusive as to the presence of a Claisen rearrangement.
Page Count
57
Department or Program
Department of Chemistry
Year Degree Awarded
1999
Copyright
Copyright 1999, all rights reserved. This open access ETD is published by Wright State University and OhioLINK.
