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Synthesis and properties of some 2,5-dihydrothiophene 1,1-dioxides

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dc.contributor.authorYen, Teh Fuen
dc.contributor.departmentChemistryen
dc.date.accessioned2014-03-14T21:08:46Zen
dc.date.adate2010-01-12en
dc.date.available2014-03-14T21:08:46Zen
dc.date.issued1955en
dc.date.rdate2010-01-12en
dc.date.sdate2010-01-12en
dc.description.abstract1. The chemical properties of 3-methyl-2, 5-dihydrothiophene 1, 1-dioxide have been studied including ionic additions, radical initiated reactions, Diels-Alder reactions, ietalation, condensation, and oxidation and reduction reactions. 2. For the first time the introduction of one halogen atom into the unsaturated five-membered cyclic sulfone without the isomerization of the double bond was accomplished. 3. The properties of 3-bromomethyl-2, 5-dihydrothiophene 1, 1-dioxide have been investigated including displacement reactions, allylic rearrangement, Diels- Alder reaction, pyrolysis and salt formation. 4. A synthesis of conjugated, substituted dienes was illustrated by the synthesis of 2-bromomethyl- 1,3-butadiene. 5. A novel Diels-Alder reaction between 3-bromomethyl and 2,5-dihydrothiophene 1, 1-dioxide has been described. 6. The structure of 3-bromomethyl-2, 5-dihydrothiophene 1, 1-dioxide was supported both by pyrolysis studies and by the above mentioned Diels-Alder reaction. The structure of the pyrolysate, 2-bromomethyl- 1,3-butadiene, was substantiated by both infrared and ultraviolet evidence. 7. Isomeric monobromo dihydrothiophene 1, 1-dioxides have been prepared via elimination reactions of the isomeric dibromo tetrahydrothiophene 1, 1-dioxides. Their structures have been supported by ultraviolet absorption studies. 8. Evidence for the allylic rearrangement of 3-bromomethyl-2, 5-dihydrothiophene 1, 1-dioxide was achieved through ultraviolet absorption studies. 9. A simple method for the identification of alkyldinydrothiophene 1, 1-dioxides was demonstrated. 10. The modified Prilezhaev oxidation has been applied to 3-methyl-2,5-dihydrothiophene 1, 1-dioxide. 11. The addition of chlorine and of hydrogen iodide to 3-methyl-2,5-dihydrothiophene 1, 1-dioxide was accomplished. 12. The formation of the quaternary salts from 3-bromnomethyl-2, 5-dihydrothiophene 1, 1-dioxide and nitrogenous bases was found to be of general application. The use of certain salts as synthetic intermediates was attempted.en
dc.description.degreePh. D.en
dc.format.extentxi, 287 leavesen
dc.format.mediumBTDen
dc.format.mimetypeapplication/pdfen
dc.identifier.otheretd-01122010-020235en
dc.identifier.sourceurlhttp://scholar.lib.vt.edu/theses/available/etd-01122010-020235/en
dc.identifier.urihttp://hdl.handle.net/10919/37189en
dc.language.isoenen
dc.publisherVirginia Techen
dc.relation.haspartLD5655.V856_1955.Y47.pdfen
dc.relation.isformatofOCLC# 20461465en
dc.rightsIn Copyrighten
dc.rights.urihttp://rightsstatements.org/vocab/InC/1.0/en
dc.subject.lccLD5655.V856 1955.Y47en
dc.subject.lcshChemical reactions -- Researchen
dc.subject.lcshDiels-Alder reaction -- Researchen
dc.titleSynthesis and properties of some 2,5-dihydrothiophene 1,1-dioxidesen
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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