Title page for ETD etd-05112010-020153

Type of Document Master's Thesis
Author Brumfield, Kimberly K
URN etd-05112010-020153
Title Synthesis of an activated difluorotetraketone monomer via Reissert chemistry
Degree Master of Science
Department Chemistry
Advisory Committee
Advisor Name Title
Gibson, Harry W. Committee Chair
McGrath, James E. Committee Member
  • Difluorotetraketone monomer
Date of Defense 1992-10-19
Availability restricted
The chemistry of Reissert compounds has been utilized to synthesize an activated difluorotetraketone monomer, 1 A-bis { 1-[ 4-(p-fluorobenzoyl)isoquinoly ] carbonyl } benzene (18). Two synthetic routes were explored in an attempt to find an efficient means of preparation. These routes entail preparation via a dibenzylic bis(isoquinoline) and a diketone bis(isoquinoline) system. These compounds were converted to their corresponding Reissert compounds. Reaction of the anion of the dibenzylic Reissert compound with p-fluorobenzaldehyde, followed by oxidation of both benzylic sites has produced the novel difluorotetraketone monomer. In addition, rearrangement of the dike tone Reissert compound has produced the novel difluorotetraketone monomer. This monomer offers a route to a novel family of poly(heteroarylene ethers).
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