Abstract
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.
Degree
thesis:*- Name thesis:degree_name
- Ph. D.
- Level thesis:degree_level
- doctoral
- Discipline thesis:degree_discipline
- Chemistry
- Department dc:contributor.department
- Chemistry
- Grantor dc:publisher
- Virginia Tech
- Year dc:date.issued
- 1990
Author and committee
dc:creator, dc:contributor.*- Author dc:creator
-
- Layman, William Joseph
- Chair dc:contributor.committeechair
-
- Wolfe, James F.
- Committee members dc:contributor.committeemember
-
- Dillard, John G.
- Dorn, Harry C.
- Hudlicky, Tomas
- Tanko, James M.
Rights
dc:rights- Statement dc:rights
-
- In Copyright
- Licence dc:rights.uri
- Language dc:language.iso
- en
Identifiers
dc:identifier.*- Dc Identifier Other
- etd-08252008-162626
- OAI identifier oai:identifier
- oai:vtechworks.lib.vt.edu:10919/39245