Studies of sodium azide with tetraphenylcyclopentadienones and various analogs

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dc.contributor.authorDavis, Edward A.en
dc.contributor.committeechairOgliaruso, Michael A.en
dc.contributor.committeememberHudlicky, Milesen
dc.contributor.committeememberMcNair, Harold M.en
dc.contributor.departmentChemistryen
dc.date.accessioned2014-03-14T21:49:37Zen
dc.date.adate2012-11-14en
dc.date.available2014-03-14T21:49:37Zen
dc.date.issued1985-11-05en
dc.date.rdate2012-11-14en
dc.date.sdate2012-11-14en
dc.description.abstractThe 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.en
dc.description.degreeMaster of Scienceen
dc.format.extentvi, 62 leavesen
dc.format.mediumBTDen
dc.format.mimetypeapplication/pdfen
dc.identifier.otheretd-11142012-040248en
dc.identifier.sourceurlhttp://scholar.lib.vt.edu/theses/available/etd-11142012-040248/en
dc.identifier.urihttp://hdl.handle.net/10919/45676en
dc.publisherVirginia Techen
dc.relation.haspartLD5655.V855_1985.D383.pdfen
dc.relation.isformatofOCLC# 13416009en
dc.rightsIn Copyrighten
dc.rights.urihttp://rightsstatements.org/vocab/InC/1.0/en
dc.subject.lccLD5655.V855 1985.D383en
dc.subject.lcshAzides -- Reactivity -- Experimentsen
dc.subject.lcshKetones -- Reactivity -- Experimentsen
dc.titleStudies of sodium azide with tetraphenylcyclopentadienones and various analogsen
dc.typeThesisen
dc.type.dcmitypeTexten
thesis.degree.disciplineChemistryen
thesis.degree.grantorVirginia Polytechnic Institute and State Universityen
thesis.degree.levelmastersen
thesis.degree.nameMaster of Scienceen

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