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Synthesis of novel heterocyclic difluoro monomers via the chemistry of reissert compounds

Activated dichloro- and difluoro- monomers are well known for the synthesis of high-performance polymeric materials through the use of aromatic nucleophilic displacement reactions. Here, novel activated difluoro monomers were synthesized using the well established chemistry of Reissert compounds.

Difunctional bis(Reissert compound)s were synthesized by the reaction of 4-(pfluorobenzylisoquinoline) and trimethylsilyl cyanide with the following diacid chlorides: sulfonylbis(p-phenyleneoxy)dibenzoy chloride, oxybis (benzoyl chloride), and sulfonylbis(benzoyl chloride}. These aforementioned compounds were rearranged using NaH/THF to produce the desired diketones. Finally, difluorotetraketone monomers were produced by oxidation of the benzylic methylenes of the diketones. These reactions were evaluated by FTI R and 1 HNMR. These new activated heterocyclic difluorotetraketones are precursors to novel heterocyclic poly(ether ketones). / Master of Science

Identiferoai:union.ndltd.org:VTETD/oai:vtechworks.lib.vt.edu:10919/42473
Date04 May 2010
CreatorsGrisle, Roger Anthony
ContributorsChemistry, Gibson, Harry W., Tanko, James M., Ward, Thomas C.
PublisherVirginia Tech
Source SetsVirginia Tech Theses and Dissertation
LanguageEnglish
Detected LanguageEnglish
TypeThesis, Text
Formatx, 89 leaves, BTD, application/pdf, application/pdf
RightsIn Copyright, http://rightsstatements.org/vocab/InC/1.0/
RelationOCLC# 30443417, LD5655.V855_1992.G757.pdf

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