{"id":{"repo_id":"uiuc","oai_identifier":"oai:www.ideals.illinois.edu:2142/70217"},"canonical_url":"https://search.dev.ndltd.org/etd/uiuc/oai:www.ideals.illinois.edu:2142/70217","repository":{"repo_id":"uiuc","name":"University of Illinois - Urbana-Champaign","base_url":"https://www.ideals.illinois.edu/oai-pmh"},"display":{"title":"Lithiation of Oxy-Arenes; New Methodology for Electrophilic Aromatic Substitutions: Attempted Synthesis of Thiaheptalenes and Heterocyclic Pyrene Systems","abstract":"Lithiation of oxy-arenes was studied. The lithiation of 4-hydroxyphenanthrene with 2 eq. of n-butyllithium/TMEDA in cyclohexane at 23(DEGREES)C occurs completely at the 5-position, although the 5-position is the most hindered position in the 4-hydroxyphenanthrene. By contrast, the lithiation of 4-methoxyphenanthrene by 1 eq. of n-BuLi/TMEDA in cyclohexane at 23(DEGREES)C occurs exclusively at the 3 position. Similarly, lithiation of (alpha)-naphthol under the same reaction condition gave 8-position lithiation and 2-hydroxybiphenyl was lithiated at the 2'-position. New reagents, 1,2-dibromo- and 1,2-dichloro-tetrafluoroethane were used for the halogenation of the lithiated positions. These remote lithiation reactions are useful in the synthesis of theoretically interesting heterocyclic heptalene and pyrene systems.","abstract_html":"Lithiation of oxy-arenes was studied. The lithiation of 4-hydroxyphenanthrene with 2 eq. of n-butyllithium/TMEDA in cyclohexane at 23(DEGREES)C occurs completely at the 5-position, although the 5-position is the most hindered position in the 4-hydroxyphenanthrene. By contrast, the lithiation of 4-methoxyphenanthrene by 1 eq. of n-BuLi/TMEDA in cyclohexane at 23(DEGREES)C occurs exclusively at the 3 position. Similarly, lithiation of (alpha)-naphthol under the same reaction condition gave 8-position lithiation and 2-hydroxybiphenyl was lithiated at the 2'-position. New reagents, 1,2-dibromo- and 1,2-dichloro-tetrafluoroethane were used for the halogenation of the lithiated positions. These remote lithiation reactions are useful in the synthesis of theoretically interesting heterocyclic heptalene and pyrene systems.","abstract_has_math":false,"creators":["Bashir Hashemi, Abdollah"],"institution":"University of Illinois at Urbana-Champaign","degree_name":"Ph.D.","degree_level":"Dissertation","degree_discipline":"Chemistry","degree_department":null,"school":null,"contributors":[],"advisors":[],"committee_chairs":[],"committee_members":[],"year":2014,"date_issued":"2014-12-15T23:17:54Z","date_published":"2014-12-15T23:17:54Z","updated_at":"2026-07-22T22:26:02Z","subjects":["Chemistry, Organic"],"languages":[],"rights":[],"rights_urls":[],"identifier_entries":[{"key":"dc:identifier","label":"Identifier","values":["(UMI)AAI8324506"],"render_values":[{"text":"(UMI)AAI8324506","href":null,"code":true}]}]},"links":{"outbound_url":"http://hdl.handle.net/2142/70217","outbound_label":"Handle","outbound_source":"dc:identifier"},"metadata_groups":[{"id":"people","label":"People","entries":[{"key":"dc:creator","label":"Author","values":["Bashir Hashemi, Abdollah"]}]},{"id":"academic_context","label":"Academic Context","entries":[{"key":"dc:date","label":"Dc Date","values":["2014-12-15T23:17:54Z","10000-01-01","1983"]},{"key":"dc:type","label":"Dc Type","values":["text"]},{"key":"thesis:degree_discipline","label":"Discipline","values":["Chemistry"]},{"key":"thesis:degree_level","label":"Degree Level","values":["Dissertation"]},{"key":"thesis:degree_name","label":"Degree Name","values":["Ph.D."]},{"key":"thesis:institution_name","label":"Thesis Institution Name","values":["University of Illinois at Urbana-Champaign"]}]},{"id":"subjects_keywords","label":"Subjects and Keywords","entries":[{"key":"dc:subject","label":"Dc Subject","values":["Chemistry, Organic"]}]},{"id":"identifiers","label":"Identifiers","entries":[{"key":"dc:identifier","label":"Identifier","values":["http://hdl.handle.net/2142/70217","(UMI)AAI8324506"]}]},{"id":"additional","label":"Additional Metadata","entries":[{"key":"dc:description","label":"Description","values":["Lithiation of oxy-arenes was studied. The lithiation of 4-hydroxyphenanthrene with 2 eq. of n-butyllithium/TMEDA in cyclohexane at 23(DEGREES)C occurs completely at the 5-position, although the 5-position is the most hindered position in the 4-hydroxyphenanthrene. By contrast, the lithiation of 4-methoxyphenanthrene by 1 eq. of n-BuLi/TMEDA in cyclohexane at 23(DEGREES)C occurs exclusively at the 3 position. Similarly, lithiation of (alpha)-naphthol under the same reaction condition gave 8-position lithiation and 2-hydroxybiphenyl was lithiated at the 2'-position. New reagents, 1,2-dibromo- and 1,2-dichloro-tetrafluoroethane were used for the halogenation of the lithiated positions. These remote lithiation reactions are useful in the synthesis of theoretically interesting heterocyclic heptalene and pyrene systems.","Made available in DSpace on 2014-12-15T23:17:54Z (GMT). No. of bitstreams: 1 8324506.pdf: 2263896 bytes, checksum: b44ffa3d9c88553b33e2361e04a621b4 (MD5) Previous issue date: 1983","Embargo set by: Seth Robbins for item 70383 Lift date: Forever Reason: Restricted to the U of I community idenfinitely during batch ingest of legacy ETDs","Restricted to the U of I community idenfinitely during batch ingest of legacy ETDs","U of I Only","78 p.","Thesis (Ph.D.)--University of Illinois at Urbana-Champaign, 1983."]},{"key":"dc:title","label":"Title","values":["Lithiation of Oxy-Arenes; New Methodology for Electrophilic Aromatic Substitutions: Attempted Synthesis of Thiaheptalenes and Heterocyclic Pyrene Systems"]}]}],"canonical_facts":{"dc:creator":["Bashir Hashemi, Abdollah"],"dc:date":["2014-12-15T23:17:54Z","10000-01-01","1983"],"dc:description":["Lithiation of oxy-arenes was studied. The lithiation of 4-hydroxyphenanthrene with 2 eq. of n-butyllithium/TMEDA in cyclohexane at 23(DEGREES)C occurs completely at the 5-position, although the 5-position is the most hindered position in the 4-hydroxyphenanthrene. By contrast, the lithiation of 4-methoxyphenanthrene by 1 eq. of n-BuLi/TMEDA in cyclohexane at 23(DEGREES)C occurs exclusively at the 3 position. Similarly, lithiation of (alpha)-naphthol under the same reaction condition gave 8-position lithiation and 2-hydroxybiphenyl was lithiated at the 2'-position. New reagents, 1,2-dibromo- and 1,2-dichloro-tetrafluoroethane were used for the halogenation of the lithiated positions. These remote lithiation reactions are useful in the synthesis of theoretically interesting heterocyclic heptalene and pyrene systems.","Made available in DSpace on 2014-12-15T23:17:54Z (GMT). No. of bitstreams: 1 8324506.pdf: 2263896 bytes, checksum: b44ffa3d9c88553b33e2361e04a621b4 (MD5) Previous issue date: 1983","Embargo set by: Seth Robbins for item 70383 Lift date: Forever Reason: Restricted to the U of I community idenfinitely during batch ingest of legacy ETDs","Restricted to the U of I community idenfinitely during batch ingest of legacy ETDs","U of I Only","78 p.","Thesis (Ph.D.)--University of Illinois at Urbana-Champaign, 1983."],"dc:identifier":["http://hdl.handle.net/2142/70217","(UMI)AAI8324506"],"dc:subject":["Chemistry, Organic"],"dc:title":["Lithiation of Oxy-Arenes; New Methodology for Electrophilic Aromatic Substitutions: Attempted Synthesis of Thiaheptalenes and Heterocyclic Pyrene Systems"],"dc:type":["text"],"thesis:degree_discipline":["Chemistry"],"thesis:degree_level":["Dissertation"],"thesis:degree_name":["Ph.D."],"thesis:institution_name":["University of Illinois at Urbana-Champaign"]},"updated_at":"2026-07-22T22:26:02Z"}