{"id":{"repo_id":"uiuc","oai_identifier":"oai:www.ideals.illinois.edu:2142/20053"},"canonical_url":"https://search.dev.ndltd.org/etd/uiuc/oai:www.ideals.illinois.edu:2142/20053","repository":{"repo_id":"uiuc","name":"University of Illinois - Urbana-Champaign","base_url":"https://www.ideals.illinois.edu/oai-pmh"},"display":{"title":"Synthetic methods and studies of some 10-Y-5 and 12-Y-6 hypervalent main group element species of group IIIB","abstract":"N,N,N-tributylbutanaminium(OC-6-11$\\sp\\prime$)-bis (4-(1,1-dimethylethyl)-$\\alpha,\\alpha,\\alpha\\sp\\prime\\alpha\\sp\\prime$-tetrakis(trifluoromethyl)-2,6-pyridinedimethanolato(2-)N1,O$\\alpha$,O$\\alpha\\sp\\prime$) aluminum, a 12-Al-6 anionic species was synthesized and experimentally examined. Neutral mono-protonated and mono-methylated products of this anion were synthesized and studied. X-ray crystallography was used to establish the structure of the octahedral 12-Al-6 species and its protonated analogue. The protonated species was a distorted octahedral species with the proton hydrogen-bonding two of the apical oxygens.","abstract_html":"N,N,N-tributylbutanaminium(OC-6-11$\\sp\\prime$)-bis (4-(1,1-dimethylethyl)-<span class=\"etd-inline-math\">&alpha;,&alpha;,&alpha;\\sp\\prime&alpha;\\sp\\prime</span>-tetrakis(trifluoromethyl)-2,6-pyridinedimethanolato(2-)N1,O<span class=\"etd-inline-math\">&alpha;</span>,O<span class=\"etd-inline-math\">&alpha;\\sp\\prime</span>) aluminum, a 12-Al-6 anionic species was synthesized and experimentally examined. Neutral mono-protonated and mono-methylated products of this anion were synthesized and studied. X-ray crystallography was used to establish the structure of the octahedral 12-Al-6 species and its protonated analogue. The protonated species was a distorted octahedral species with the proton hydrogen-bonding two of the apical oxygens.","abstract_has_math":true,"creators":["Hoglen, Dean Kent"],"institution":"University of Illinois at Urbana-Champaign","degree_name":"Ph.D.","degree_level":"Dissertation","degree_discipline":"Chemistry","degree_department":null,"school":null,"contributors":["Martin, J.C."],"advisors":[],"committee_chairs":[],"committee_members":[],"year":2011,"date_issued":"2011-05-07T12:27:18Z","date_published":"2011-05-07T12:27:18Z","updated_at":"2026-07-22T22:25:15Z","subjects":["Chemistry, Organic"],"languages":["eng"],"rights":["Copyright 1990 Hoglen, Dean Kent"],"rights_urls":[],"identifier_entries":[{"key":"dc:identifier","label":"Identifier","values":["AAI9026207","(UMI)AAI9026207"],"render_values":[{"text":"AAI9026207","href":null,"code":true},{"text":"(UMI)AAI9026207","href":null,"code":true}]}]},"links":{"outbound_url":"http://hdl.handle.net/2142/20053","outbound_label":"Handle","outbound_source":"dc:identifier"},"metadata_groups":[{"id":"people","label":"People","entries":[{"key":"dc:contributor","label":"Contributor","values":["Martin, J.C."]},{"key":"dc:creator","label":"Author","values":["Hoglen, Dean Kent"]}]},{"id":"academic_context","label":"Academic Context","entries":[{"key":"dc:date","label":"Dc Date","values":["2011-05-07T12:27:18Z","10000-01-01","1990"]},{"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":"language_rights","label":"Language and Rights","entries":[{"key":"dc:language","label":"Dc Language","values":["eng"]},{"key":"dc:rights","label":"Dc Rights","values":["Copyright 1990 Hoglen, Dean Kent"]}]},{"id":"identifiers","label":"Identifiers","entries":[{"key":"dc:identifier","label":"Identifier","values":["AAI9026207","(UMI)AAI9026207","http://hdl.handle.net/2142/20053"]}]},{"id":"additional","label":"Additional Metadata","entries":[{"key":"dc:description","label":"Description","values":["N,N,N-tributylbutanaminium(OC-6-11$\\sp\\prime$)-bis (4-(1,1-dimethylethyl)-$\\alpha,\\alpha,\\alpha\\sp\\prime\\alpha\\sp\\prime$-tetrakis(trifluoromethyl)-2,6-pyridinedimethanolato(2-)N1,O$\\alpha$,O$\\alpha\\sp\\prime$) aluminum, a 12-Al-6 anionic species was synthesized and experimentally examined. Neutral mono-protonated and mono-methylated products of this anion were synthesized and studied. X-ray crystallography was used to establish the structure of the octahedral 12-Al-6 species and its protonated analogue. The protonated species was a distorted octahedral species with the proton hydrogen-bonding two of the apical oxygens.","p-t-Butylhexafluorocumylthiol and N,N-dimethylhexafluorocumylamine were synthesized and found not to undergo ortho-lithiation. p-t-Butylhexafluorocumylthiol forms several products upon treatment with an alkyllithium reagent and N,N-dimethylhexafluorocumylamine undergoes meta-lithiation upon treatment with sec-butyllithium in the presence of TMEDA. Evidence for the formation of stable hypervalent phosphorus and silicon species using 1,3-bis(2$\\sp\\prime$-pyridylimino)isoindoline as a tridentate ligand was obtained.","New synthetic routes were developed for 4-t-butyl-2,6-bis(1-hydroxy-1-trifluoromethyl-2,2,2-trifluoroethyl)pyridine and 2-amino-4-(t-butyl)pyridine which allowed their synthesis on a large scale, with reasonable amounts formed. The former was synthesized by ortho-lithiation of 4-t-butyl-2-(1-hydroxy-1-trifluoromethyl-2,2,2-trifluoroethyl)-pyridine-1-oxide and treatment with hexafluoroacetone. The latter was synthesized by nucleophilic aromatic substitution on 2-bromo-4-t-butylpyridine using sodium amide as nucleophile.","Because a new melting point reflecting a new crystal structure for 10-t-butyl-1-chloro-3,3,7,7-tetrakis(trifluoromethyl)-4,6-benzo-5-azonia-1-borata-2,8-dioxabicyclo- (3,3,0) octane resulted in a change in solubility and reactivity, new routes to hypervalent 12-B-6 and 10-B-5 species were explored, and were not successful.","Made available in DSpace on 2011-05-07T12:27:18Z (GMT). No. of bitstreams: 2 license.txt: 4922 bytes, checksum: 910b249b4beec47e7ab768910c8f966f (MD5) 9026207.pdf: 7221885 bytes, checksum: b78a61f812db7fcda03d38f99f3d5b7d (MD5) Previous issue date: 1990","Item marked as restricted to the 'UIUC Users [automated]' Group (id=2) by Howard Ding (hding2@illinois.edu) on 2011-05-07T14:41:14Z Item is restricted indefinitely.","Restriction data tranferred 2014-07-01T11:17:48-05:00 Original Data Group with Access UIUC Users [automated] Release Date: none Reason: ETDs are only available to UIUC Users without author permission","ETDs are only available to UIUC Users without author permission","U of I Only"]},{"key":"dc:title","label":"Title","values":["Synthetic methods and studies of some 10-Y-5 and 12-Y-6 hypervalent main group element species of group IIIB"]}]}],"canonical_facts":{"dc:contributor":["Martin, J.C."],"dc:creator":["Hoglen, Dean Kent"],"dc:date":["2011-05-07T12:27:18Z","10000-01-01","1990"],"dc:description":["N,N,N-tributylbutanaminium(OC-6-11$\\sp\\prime$)-bis (4-(1,1-dimethylethyl)-$\\alpha,\\alpha,\\alpha\\sp\\prime\\alpha\\sp\\prime$-tetrakis(trifluoromethyl)-2,6-pyridinedimethanolato(2-)N1,O$\\alpha$,O$\\alpha\\sp\\prime$) aluminum, a 12-Al-6 anionic species was synthesized and experimentally examined. Neutral mono-protonated and mono-methylated products of this anion were synthesized and studied. X-ray crystallography was used to establish the structure of the octahedral 12-Al-6 species and its protonated analogue. The protonated species was a distorted octahedral species with the proton hydrogen-bonding two of the apical oxygens.","p-t-Butylhexafluorocumylthiol and N,N-dimethylhexafluorocumylamine were synthesized and found not to undergo ortho-lithiation. p-t-Butylhexafluorocumylthiol forms several products upon treatment with an alkyllithium reagent and N,N-dimethylhexafluorocumylamine undergoes meta-lithiation upon treatment with sec-butyllithium in the presence of TMEDA. Evidence for the formation of stable hypervalent phosphorus and silicon species using 1,3-bis(2$\\sp\\prime$-pyridylimino)isoindoline as a tridentate ligand was obtained.","New synthetic routes were developed for 4-t-butyl-2,6-bis(1-hydroxy-1-trifluoromethyl-2,2,2-trifluoroethyl)pyridine and 2-amino-4-(t-butyl)pyridine which allowed their synthesis on a large scale, with reasonable amounts formed. The former was synthesized by ortho-lithiation of 4-t-butyl-2-(1-hydroxy-1-trifluoromethyl-2,2,2-trifluoroethyl)-pyridine-1-oxide and treatment with hexafluoroacetone. The latter was synthesized by nucleophilic aromatic substitution on 2-bromo-4-t-butylpyridine using sodium amide as nucleophile.","Because a new melting point reflecting a new crystal structure for 10-t-butyl-1-chloro-3,3,7,7-tetrakis(trifluoromethyl)-4,6-benzo-5-azonia-1-borata-2,8-dioxabicyclo- (3,3,0) octane resulted in a change in solubility and reactivity, new routes to hypervalent 12-B-6 and 10-B-5 species were explored, and were not successful.","Made available in DSpace on 2011-05-07T12:27:18Z (GMT). No. of bitstreams: 2 license.txt: 4922 bytes, checksum: 910b249b4beec47e7ab768910c8f966f (MD5) 9026207.pdf: 7221885 bytes, checksum: b78a61f812db7fcda03d38f99f3d5b7d (MD5) Previous issue date: 1990","Item marked as restricted to the 'UIUC Users [automated]' Group (id=2) by Howard Ding (hding2@illinois.edu) on 2011-05-07T14:41:14Z Item is restricted indefinitely.","Restriction data tranferred 2014-07-01T11:17:48-05:00 Original Data Group with Access UIUC Users [automated] Release Date: none Reason: ETDs are only available to UIUC Users without author permission","ETDs are only available to UIUC Users without author permission","U of I Only"],"dc:identifier":["AAI9026207","(UMI)AAI9026207","http://hdl.handle.net/2142/20053"],"dc:language":["eng"],"dc:rights":["Copyright 1990 Hoglen, Dean Kent"],"dc:subject":["Chemistry, Organic"],"dc:title":["Synthetic methods and studies of some 10-Y-5 and 12-Y-6 hypervalent main group element species of group IIIB"],"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":"2026-07-22T22:25:15Z"}