Title page for ETD etd-05042010-020216

Type of Document Master's Thesis
Author Grisle, Roger Anthony
URN etd-05042010-020216
Title Synthesis of novel heterocyclic difluoro monomers via the chemistry of reissert compounds
Degree Master of Science
Department Chemistry
Advisory Committee
Advisor Name Title
Gibson, Harry W. Committee Chair
Tanko, James M. Committee Member
Ward, Thomas C. Committee Member
  • Heterocyclic compounds
Date of Defense 1992-10-15
Availability restricted

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).

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