A study of the electronic effects of various substituents on the course of an aromatic cyclodehydration reaction vs. a Elbs-type reaction

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dc.contributor.authorThornton, James Roberten
dc.contributor.committeechairVingiello, Frank A.en
dc.contributor.departmentChemistryen
dc.date.accessioned2014-03-14T21:23:42Zen
dc.date.adate2009-12-23en
dc.date.available2014-03-14T21:23:42Zen
dc.date.issued1963en
dc.date.rdate2009-12-23en
dc.date.sdate2009-12-23en
dc.description.abstractThe acld-oata17zed oyclodehydrat1on reaction of 2-benzylphenyl l-naphthyl ketone gives two products! 9-(1-naphthyl)anthracene, the expected product and in addition lO-phenyl-l,2-benzanthracene. This second product is the one expected it the ketone were subjected to the conditions of an .Elba reaction. The effect of substituents on the course of this reaction was investigated by synthesizing six 2-benzylphenyl 1- and 2-naphthyl ketones and subjecting each of them to the acid catalyzed reaction and to Elba reaction conditions. Of the six ketones, two had unsubstituted benzyl groups, two had 3'-methyl groups in the benzyl group and the remaining two had ,'-tr1fluoromethyl groups. The original finding was confirmed and the other ketones that cyoilzed by either treatment gave the expected products. When 2-(3'-methylbenzyl) 2-naphthl1 ketone was subjected to Elbs reaction conditions, 9-(2-naphthyl)anthraoene, the product of aromatic oyclodehydrat1on, was obtained. An explanation oft the unusual experimental results is suggested. The results of treat1ng the ketones w1th alumina and w1th l1qu1d hydrogen fluoride are reported.en
dc.description.degreePh. D.en
dc.format.extentv, 100 leavesen
dc.format.mediumBTDen
dc.format.mimetypeapplication/pdfen
dc.identifier.otheretd-12232009-020703en
dc.identifier.sourceurlhttp://scholar.lib.vt.edu/theses/available/etd-12232009-020703/en
dc.identifier.urihttp://hdl.handle.net/10919/40478en
dc.language.isoenen
dc.publisherVirginia Techen
dc.relation.haspartLD5655.V856_1963.T467.pdfen
dc.relation.isformatofOCLC# 20276215en
dc.rightsIn Copyrighten
dc.rights.urihttp://rightsstatements.org/vocab/InC/1.0/en
dc.subject.lccLD5655.V856 1963.T467en
dc.subject.lcshAromatic compounds -- Reactivity -- Experimentsen
dc.subject.lcshKetones -- Reactivity -- Experimentsen
dc.titleA study of the electronic effects of various substituents on the course of an aromatic cyclodehydration reaction vs. a Elbs-type reactionen
dc.typeDissertationen
dc.type.dcmitypeTexten
thesis.degree.disciplineChemistryen
thesis.degree.grantorVirginia Polytechnic Institute and State Universityen
thesis.degree.leveldoctoralen
thesis.degree.namePh. D.en

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