Synthesis of an activated difluorotetraketone monomer via Reissert chemistry

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).

Name thesis:degree_name

Master of Science

Level thesis:degree_level

masters

Discipline thesis:degree_discipline

Chemistry

Department dc:contributor.department

Chemistry

Grantor dc:publisher

Virginia Tech

Year dc:date.issued

1992

Author dc:creator

• Brumfield, Kimberly K.

Chair dc:contributor.committeechair

• Gibson, Harry W.

Committee member dc:contributor.committeemember

• McGrath, James E.

Statement dc:rights

• In Copyright

Licence dc:rights.uri

• http://rightsstatements.org/vocab/InC/1.0/

Language dc:language.iso

en

Dc Identifier Other

etd-05112010-020153

OAI identifier oai:identifier

oai:vtechworks.lib.vt.edu:10919/42611