{"id":{"repo_id":"uiuc","oai_identifier":"oai:www.ideals.illinois.edu:2142/70354"},"canonical_url":"https://search.dev.ndltd.org/etd/uiuc/oai:www.ideals.illinois.edu:2142/70354","repository":{"repo_id":"uiuc","name":"University of Illinois - Urbana-Champaign","base_url":"https://www.ideals.illinois.edu/oai-pmh"},"display":{"title":"I. Hexaiodobenzene Dication: A Ten-Electron Sigma-Delocalized Huckel-Aromatic Species. Ii. Synthesis and Study of Ortho-Bridged Triarylmethyl Compounds (Lithiation)","abstract":"The synthesis of the bis trifluoromethanesulfonate salt of hexaiodobenzene dication is described. Experimental evidence supports the postulate that it is a ten-electron sigma-delocalized Huckel-aromatic species.","abstract_html":"The synthesis of the bis trifluoromethanesulfonate salt of hexaiodobenzene dication is described. Experimental evidence supports the postulate that it is a ten-electron sigma-delocalized Huckel-aromatic species.","abstract_has_math":false,"creators":["Sagl, Dennis Joseph"],"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":"2014-12-15T23:18:53Z","date_published":"2014-12-15T23:18:53Z","updated_at":"2026-07-22T22:26:02Z","subjects":["Chemistry, Organic"],"languages":[],"rights":[],"rights_urls":[],"identifier_entries":[{"key":"dc:identifier","label":"Identifier","values":["(UMI)AAI8701604"],"render_values":[{"text":"(UMI)AAI8701604","href":null,"code":true}]}]},"links":{"outbound_url":"http://hdl.handle.net/2142/70354","outbound_label":"Handle","outbound_source":"dc:identifier"},"metadata_groups":[{"id":"people","label":"People","entries":[{"key":"dc:creator","label":"Author","values":["Sagl, Dennis Joseph"]}]},{"id":"academic_context","label":"Academic Context","entries":[{"key":"dc:date","label":"Dc Date","values":["2014-12-15T23:18:53Z","10000-01-01","1986"]},{"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/2142/70354","(UMI)AAI8701604"]}]},{"id":"additional","label":"Additional Metadata","entries":[{"key":"dc:description","label":"Description","values":["The synthesis of the bis trifluoromethanesulfonate salt of hexaiodobenzene dication is described. Experimental evidence supports the postulate that it is a ten-electron sigma-delocalized Huckel-aromatic species.","Syntheses of mono- and tri-tert-butyl substituted triphenylmethyl compounds with carbonyl groups bridging the ortho positions are described. Studies of the anions and radicals are described which indicate that the planarity enforced on these triphenylmethyl systems by the ortho-bridges and the (pi)-acceptor character of the carbonyl bridges give them unusual stability; furthermore, the tert-butyl groups provide increased solubility over the unsubstituted analogues. The isolation and properties of the first ionic hexaarylethane are also described.","The regiospecific lithiation of benzene rings ortho to various directing groups is a powerful synthetic method. The polylithiation of di- and triphenylmethanols and the reaction of the lithiated species with various electrophiles is described. The possible structures of the polylithiated intermediates is discussed in light of current theory regarding polylithio carbanions.","Made available in DSpace on 2014-12-15T23:18:53Z (GMT). No. of bitstreams: 1 8701604.pdf: 3495436 bytes, checksum: 91356999e61d98cb10fc0821b19b8cf3 (MD5) Previous issue date: 1986","Embargo set by: Seth Robbins for item 70520 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","111 p.","Thesis (Ph.D.)--University of Illinois at Urbana-Champaign, 1986."]},{"key":"dc:title","label":"Title","values":["I. Hexaiodobenzene Dication: A Ten-Electron Sigma-Delocalized Huckel-Aromatic Species. Ii. Synthesis and Study of Ortho-Bridged Triarylmethyl Compounds (Lithiation)"]}]}],"canonical_facts":{"dc:creator":["Sagl, Dennis Joseph"],"dc:date":["2014-12-15T23:18:53Z","10000-01-01","1986"],"dc:description":["The synthesis of the bis trifluoromethanesulfonate salt of hexaiodobenzene dication is described. Experimental evidence supports the postulate that it is a ten-electron sigma-delocalized Huckel-aromatic species.","Syntheses of mono- and tri-tert-butyl substituted triphenylmethyl compounds with carbonyl groups bridging the ortho positions are described. Studies of the anions and radicals are described which indicate that the planarity enforced on these triphenylmethyl systems by the ortho-bridges and the (pi)-acceptor character of the carbonyl bridges give them unusual stability; furthermore, the tert-butyl groups provide increased solubility over the unsubstituted analogues. The isolation and properties of the first ionic hexaarylethane are also described.","The regiospecific lithiation of benzene rings ortho to various directing groups is a powerful synthetic method. The polylithiation of di- and triphenylmethanols and the reaction of the lithiated species with various electrophiles is described. The possible structures of the polylithiated intermediates is discussed in light of current theory regarding polylithio carbanions.","Made available in DSpace on 2014-12-15T23:18:53Z (GMT). No. of bitstreams: 1 8701604.pdf: 3495436 bytes, checksum: 91356999e61d98cb10fc0821b19b8cf3 (MD5) Previous issue date: 1986","Embargo set by: Seth Robbins for item 70520 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","111 p.","Thesis (Ph.D.)--University of Illinois at Urbana-Champaign, 1986."],"dc:identifier":["http://hdl.handle.net/2142/70354","(UMI)AAI8701604"],"dc:subject":["Chemistry, Organic"],"dc:title":["I. Hexaiodobenzene Dication: A Ten-Electron Sigma-Delocalized Huckel-Aromatic Species. Ii. Synthesis and Study of Ortho-Bridged Triarylmethyl Compounds (Lithiation)"],"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"}