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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