{"id":{"repo_id":"vt","oai_identifier":"oai:vtechworks.lib.vt.edu:10919/42611"},"canonical_url":"https://search.dev.ndltd.org/etd/vt/oai:vtechworks.lib.vt.edu:10919/42611","repository":{"repo_id":"vt","name":"Virginia Tech","base_url":"https://vtechworks.lib.vt.edu/oai/request"},"display":{"title":"Synthesis of an activated difluorotetraketone monomer via Reissert chemistry","abstract":"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).","abstract_html":"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).","abstract_has_math":false,"creators":["Brumfield, Kimberly K."],"institution":"Virginia Tech","degree_name":"Master of Science","degree_level":"masters","degree_discipline":"Chemistry","degree_department":"Chemistry","school":null,"contributors":[],"advisors":[],"committee_chairs":["Gibson, Harry W."],"committee_members":["McGrath, James E."],"year":1992,"date_issued":"1992-10-19","date_published":"1992-10-19","updated_at":"2026-07-22T22:19:49Z","subjects":[],"languages":["en"],"rights":["In Copyright"],"rights_urls":["http://rightsstatements.org/vocab/InC/1.0/"],"identifier_entries":[{"key":"dc:identifier.other","label":"Dc Identifier Other","values":["etd-05112010-020153"],"render_values":[{"text":"etd-05112010-020153","href":null,"code":true}]}]},"links":{"outbound_url":"http://hdl.handle.net/10919/42611","outbound_label":"Handle","outbound_source":"dc:identifier.uri"},"metadata_groups":[{"id":"people","label":"People","entries":[{"key":"dc:contributor.committeechair","label":"Committee Chair","values":["Gibson, Harry W."]},{"key":"dc:contributor.committeemember","label":"Committee Member","values":["McGrath, James E."]},{"key":"dc:contributor.department","label":"Department","values":["Chemistry"]},{"key":"dc:creator","label":"Author","values":["Brumfield, Kimberly K."]}]},{"id":"academic_context","label":"Academic Context","entries":[{"key":"dc:date.accessioned","label":"Dc Date Accessioned","values":["2014-03-14T21:36:04Z"]},{"key":"dc:date.available","label":"Dc Date Available","values":["2014-03-14T21:36:04Z","2010-05-11"]},{"key":"dc:date.issued","label":"Date","values":["1992-10-19"]},{"key":"dc:publisher","label":"Institution","values":["Virginia Tech"]},{"key":"dc:type","label":"Dc Type","values":["Thesis"]},{"key":"dc:type.dcmitype","label":"Dc Type Dcmitype","values":["Text"]},{"key":"thesis:degree_discipline","label":"Discipline","values":["Chemistry"]},{"key":"thesis:degree_level","label":"Degree Level","values":["masters"]},{"key":"thesis:degree_name","label":"Degree Name","values":["Master of Science"]},{"key":"thesis:institution_name","label":"Thesis Institution Name","values":["Virginia Polytechnic Institute and State University"]}]},{"id":"language_rights","label":"Language and Rights","entries":[{"key":"dc:language.iso","label":"Language (ISO)","values":["en"]},{"key":"dc:rights","label":"Dc Rights","values":["In Copyright"]},{"key":"dc:rights.uri","label":"Rights URI","values":["http://rightsstatements.org/vocab/InC/1.0/"]}]},{"id":"identifiers","label":"Identifiers","entries":[{"key":"dc:identifier.other","label":"Dc Identifier Other","values":["etd-05112010-020153"]},{"key":"dc:identifier.uri","label":"Identifier URI","values":["http://hdl.handle.net/10919/42611"]}]},{"id":"additional","label":"Additional Metadata","entries":[{"key":"dc:description.abstract","label":"Abstract","values":["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)."]},{"key":"dc:description.degree","label":"Dc Description Degree","values":["Master of Science"]},{"key":"dc:format.medium","label":"Dc Format Medium","values":["BTD"]},{"key":"dc:format.mimetype","label":"Dc Format Mimetype","values":["application/pdf"]},{"key":"dc:title","label":"Title","values":["Synthesis of an activated difluorotetraketone monomer via Reissert chemistry"]}]}],"canonical_facts":{"dc:contributor.committeechair":["Gibson, Harry W."],"dc:contributor.committeemember":["McGrath, James E."],"dc:contributor.department":["Chemistry"],"dc:creator":["Brumfield, Kimberly K."],"dc:date.accessioned":["2014-03-14T21:36:04Z"],"dc:date.available":["2014-03-14T21:36:04Z","2010-05-11"],"dc:date.issued":["1992-10-19"],"dc:description.abstract":["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. 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