{"id":{"repo_id":"vt","oai_identifier":"oai:vtechworks.lib.vt.edu:10919/45676"},"canonical_url":"https://search.dev.ndltd.org/etd/vt/oai:vtechworks.lib.vt.edu:10919/45676","repository":{"repo_id":"vt","name":"Virginia Tech","base_url":"https://vtechworks.lib.vt.edu/oai/request"},"display":{"title":"Studies of sodium azide with tetraphenylcyclopentadienones and various analogs","abstract":"The reaction of sodium azide with 2-p-chloro- and 2-p–methoxyphenyl–3,4,5-triphenyl–2,4-cyclopentadien– Iâ one was studied to determine if the substituent would have any appreciable effect on the product distribution of the corresponding l,5,7,8–tetraphenyl-2,3,4–triazabicyclo[3.3.0]octa-2,7-dien-6-ones and the 3,4,5,6–tetraphenyl–2(lH)â pyridinones that were formed by an acid catalyzed rearrangement. It was found that the chloro substituent had no effect on the reaction. The methoxy substituent had a moderate effect in that the product arising from the stabilized intermediate cation was favored by a ratio of approximately 3 to l. The two simple linear analogs studied were l,2,3,3–tetraphenyl-2-propen-l-one and 3,4,4-triphenyl-3–buten–2â one. These compounds did not react with azide, presumably due to charge delocalization. Also studied as a cyclic analog was 2,7-diphenyltropone which did not react due to the aromatic character of the tropone ring system. A reaction did occur with diphenylcyclopropenone to give an unidentified product. However, the reaction did not take place in the same fashion as for the tetracyclones.","abstract_html":"The reaction of sodium azide with 2-p-chloro- and 2-p–methoxyphenyl–3,4,5-triphenyl–2,4-cyclopentadien– Iâ one was studied to determine if the substituent would have any appreciable effect on the product distribution of the corresponding l,5,7,8–tetraphenyl-2,3,4–triazabicyclo[3.3.0]octa-2,7-dien-6-ones and the 3,4,5,6–tetraphenyl–2(lH)â pyridinones that were formed by an acid catalyzed rearrangement. It was found that the chloro substituent had no effect on the reaction. The methoxy substituent had a moderate effect in that the product arising from the stabilized intermediate cation was favored by a ratio of approximately 3 to l. The two simple linear analogs studied were l,2,3,3–tetraphenyl-2-propen-l-one and 3,4,4-triphenyl-3–buten–2â one. These compounds did not react with azide, presumably due to charge delocalization. Also studied as a cyclic analog was 2,7-diphenyltropone which did not react due to the aromatic character of the tropone ring system. A reaction did occur with diphenylcyclopropenone to give an unidentified product. However, the reaction did not take place in the same fashion as for the tetracyclones.","abstract_has_math":false,"creators":["Davis, Edward A."],"institution":"Virginia Tech","degree_name":"Master of Science","degree_level":"masters","degree_discipline":"Chemistry","degree_department":"Chemistry","school":null,"contributors":[],"advisors":[],"committee_chairs":["Ogliaruso, Michael A."],"committee_members":["Hudlicky, Miles","McNair, Harold M."],"year":1985,"date_issued":"1985-11-05","date_published":"1985-11-05","updated_at":"2026-07-24T05:56:46Z","subjects":[],"languages":[],"rights":["In Copyright"],"rights_urls":["http://rightsstatements.org/vocab/InC/1.0/"],"identifier_entries":[{"key":"dc:identifier.other","label":"Dc Identifier Other","values":["etd-11142012-040248"],"render_values":[{"text":"etd-11142012-040248","href":null,"code":true}]}]},"links":{"outbound_url":"http://hdl.handle.net/10919/45676","outbound_label":"Handle","outbound_source":"dc:identifier.uri"},"metadata_groups":[{"id":"people","label":"People","entries":[{"key":"dc:contributor.committeechair","label":"Committee Chair","values":["Ogliaruso, Michael A."]},{"key":"dc:contributor.committeemember","label":"Committee Member","values":["Hudlicky, Miles","McNair, Harold M."]},{"key":"dc:contributor.department","label":"Department","values":["Chemistry"]},{"key":"dc:creator","label":"Author","values":["Davis, Edward A."]}]},{"id":"academic_context","label":"Academic Context","entries":[{"key":"dc:date.accessioned","label":"Dc Date Accessioned","values":["2014-03-14T21:49:37Z"]},{"key":"dc:date.available","label":"Dc Date Available","values":["2014-03-14T21:49:37Z","2012-11-14"]},{"key":"dc:date.issued","label":"Date","values":["1985-11-05"]},{"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: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-11142012-040248"]},{"key":"dc:identifier.uri","label":"Identifier URI","values":["http://hdl.handle.net/10919/45676"]}]},{"id":"additional","label":"Additional Metadata","entries":[{"key":"dc:description.abstract","label":"Abstract","values":["The reaction of sodium azide with 2-p-chloro- and 2-p–methoxyphenyl–3,4,5-triphenyl–2,4-cyclopentadien– Iâ one was studied to determine if the substituent would have any appreciable effect on the product distribution of the corresponding l,5,7,8–tetraphenyl-2,3,4–triazabicyclo[3.3.0]octa-2,7-dien-6-ones and the 3,4,5,6–tetraphenyl–2(lH)â pyridinones that were formed by an acid catalyzed rearrangement. It was found that the chloro substituent had no effect on the reaction. The methoxy substituent had a moderate effect in that the product arising from the stabilized intermediate cation was favored by a ratio of approximately 3 to l. The two simple linear analogs studied were l,2,3,3–tetraphenyl-2-propen-l-one and 3,4,4-triphenyl-3–buten–2â one. These compounds did not react with azide, presumably due to charge delocalization. Also studied as a cyclic analog was 2,7-diphenyltropone which did not react due to the aromatic character of the tropone ring system. A reaction did occur with diphenylcyclopropenone to give an unidentified product. However, the reaction did not take place in the same fashion as for the tetracyclones."]},{"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":["Studies of sodium azide with tetraphenylcyclopentadienones and various analogs"]}]}],"canonical_facts":{"dc:contributor.committeechair":["Ogliaruso, Michael A."],"dc:contributor.committeemember":["Hudlicky, Miles","McNair, Harold M."],"dc:contributor.department":["Chemistry"],"dc:creator":["Davis, Edward A."],"dc:date.accessioned":["2014-03-14T21:49:37Z"],"dc:date.available":["2014-03-14T21:49:37Z","2012-11-14"],"dc:date.issued":["1985-11-05"],"dc:description.abstract":["The reaction of sodium azide with 2-p-chloro- and 2-p–methoxyphenyl–3,4,5-triphenyl–2,4-cyclopentadien– Iâ one was studied to determine if the substituent would have any appreciable effect on the product distribution of the corresponding l,5,7,8–tetraphenyl-2,3,4–triazabicyclo[3.3.0]octa-2,7-dien-6-ones and the 3,4,5,6–tetraphenyl–2(lH)â pyridinones that were formed by an acid catalyzed rearrangement. It was found that the chloro substituent had no effect on the reaction. The methoxy substituent had a moderate effect in that the product arising from the stabilized intermediate cation was favored by a ratio of approximately 3 to l. The two simple linear analogs studied were l,2,3,3–tetraphenyl-2-propen-l-one and 3,4,4-triphenyl-3–buten–2â one. These compounds did not react with azide, presumably due to charge delocalization. Also studied as a cyclic analog was 2,7-diphenyltropone which did not react due to the aromatic character of the tropone ring system. A reaction did occur with diphenylcyclopropenone to give an unidentified product. However, the reaction did not take place in the same fashion as for the tetracyclones."],"dc:description.degree":["Master of Science"],"dc:format.medium":["BTD"],"dc:format.mimetype":["application/pdf"],"dc:identifier.other":["etd-11142012-040248"],"dc:identifier.uri":["http://hdl.handle.net/10919/45676"],"dc:publisher":["Virginia Tech"],"dc:rights":["In Copyright"],"dc:rights.uri":["http://rightsstatements.org/vocab/InC/1.0/"],"dc:title":["Studies of sodium azide with tetraphenylcyclopentadienones and various analogs"],"dc:type":["Thesis"],"dc:type.dcmitype":["Text"],"thesis:degree_discipline":["Chemistry"],"thesis:degree_level":["masters"],"thesis:degree_name":["Master of Science"],"thesis:institution_name":["Virginia Polytechnic Institute and State University"]},"updated_at":"2026-07-24T05:56:46Z"}