The SRN1 reactivity of halobenzenesulfonamides and related compounds

dc.contributor.authorLayman, William Josephen
dc.contributor.committeechairWolf, James F.en
dc.contributor.committeememberDillard, John G.en
dc.contributor.committeememberDorn, Harry C.en
dc.contributor.committeememberHudlicky, Tomasen
dc.contributor.committeememberTanko, James M.en
dc.contributor.departmentChemistryen
dc.date.accessioned2014-03-14T21:18:15Zen
dc.date.adate2008-08-25en
dc.date.available2014-03-14T21:18:15Zen
dc.date.issued1990-09-15en
dc.date.rdate2008-08-25en
dc.date.sdate2008-08-25en
dc.description.abstractAn investigation of the application of nucleophilic aromatic substitution by the SRN 1 mechanism of halobenzenesulfonamides and related compounds towards the synthesis of 1,2-benzothiazine I,I-dioxides is reported. 3-Substituted and 3,4- disubstituted 2<i>H</i>-l,2-benzothiazine l,l-dioxides were prepared in moderate to good yields via the photostimulated reaction of 2-halobenzenesulfonamides with ketone enolates. It was observed that with certain ketone enolates reduction to yield benzene sulfonamide competed with the substitution reaction. The presence of β-hydrogen atoms was a common structural feature of ketones used in reactions in which reduction competed with substitution. It was also observed that the amount of reduction product isolated increased as a function of the number of β-hydrogen atoms present on the ketone enolate. It was found that 2-bromo and 2-iodobenzenesulfonamide exhibit comparable reactivity with ketone enolates that do not possess β-hydrogen atoms. However, a marked decrease in the reactivity of 2-bromobenzenesulfonamide was observed when β-hydrogen atoms were present on the ketone enolate.en
dc.description.degreePh. D.en
dc.format.extentvii, 219 leavesen
dc.format.mediumBTDen
dc.format.mimetypeapplication/pdfen
dc.identifier.otheretd-08252008-162626en
dc.identifier.sourceurlhttp://scholar.lib.vt.edu/theses/available/etd-08252008-162626/en
dc.identifier.urihttp://hdl.handle.net/10919/39245en
dc.language.isoenen
dc.publisherVirginia Techen
dc.relation.haspartLD5655.V856_1990.L396.pdfen
dc.relation.isformatofOCLC# 23657995en
dc.rightsIn Copyrighten
dc.rights.urihttp://rightsstatements.org/vocab/InC/1.0/en
dc.subject.lccLD5655.V856 1990.L396en
dc.subject.lcshHeterocyclic compoundsen
dc.titleThe SRN1 reactivity of halobenzenesulfonamides and related compoundsen
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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