{"id":{"repo_id":"vt","oai_identifier":"oai:vtechworks.lib.vt.edu:10919/39245"},"canonical_url":"https://search.dev.ndltd.org/etd/vt/oai:vtechworks.lib.vt.edu:10919/39245","repository":{"repo_id":"vt","name":"Virginia Tech","base_url":"https://vtechworks.lib.vt.edu/oai/request"},"display":{"title":"The SRN1 reactivity of halobenzenesulfonamides and related compounds","abstract":"An 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.","abstract_html":"An 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&lt;i&gt;H&lt;/i&gt;-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.","abstract_has_math":false,"creators":["Layman, William Joseph"],"institution":"Virginia Tech","degree_name":"Ph. 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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."]},{"key":"dc:description.degree","label":"Dc Description Degree","values":["Ph. D."]},{"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":["The SRN1 reactivity of halobenzenesulfonamides and related compounds"]}]}],"canonical_facts":{"dc:contributor.committeechair":["Wolfe, James F."],"dc:contributor.committeemember":["Dillard, John G.","Dorn, Harry C.","Hudlicky, Tomas","Tanko, James M."],"dc:contributor.department":["Chemistry"],"dc:creator":["Layman, William Joseph"],"dc:date.accessioned":["2014-03-14T21:18:15Z"],"dc:date.available":["2014-03-14T21:18:15Z","2008-08-25"],"dc:date.issued":["1990-09-15"],"dc:description.abstract":["An 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."],"dc:description.degree":["Ph. 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