{"id":{"repo_id":"vt","oai_identifier":"oai:vtechworks.lib.vt.edu:10919/37189"},"canonical_url":"https://search.dev.ndltd.org/etd/vt/oai:vtechworks.lib.vt.edu:10919/37189","repository":{"repo_id":"vt","name":"Virginia Tech","base_url":"https://vtechworks.lib.vt.edu/oai/request"},"display":{"title":"Synthesis and properties of some 2,5-dihydrothiophene 1,1-dioxides","abstract":"1. 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.","abstract_html":"1. 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.","abstract_has_math":false,"creators":["Yen, Teh Fu"],"institution":"Virginia Tech","degree_name":"Ph. D.","degree_level":"doctoral","degree_discipline":"Chemistry","degree_department":"Chemistry","school":null,"contributors":[],"advisors":[],"committee_chairs":[],"committee_members":[],"year":1955,"date_issued":"1955","date_published":"1955","updated_at":"2026-07-22T22:19:00Z","subjects":[],"languages":["en"],"rights":["In Copyright"],"rights_urls":["http://rightsstatements.org/vocab/InC/1.0/"],"identifier_entries":[{"key":"dc:identifier.other","label":"Dc Identifier Other","values":["etd-01122010-020235"],"render_values":[{"text":"etd-01122010-020235","href":null,"code":true}]}]},"links":{"outbound_url":"http://hdl.handle.net/10919/37189","outbound_label":"Handle","outbound_source":"dc:identifier.uri"},"metadata_groups":[{"id":"people","label":"People","entries":[{"key":"dc:contributor.department","label":"Department","values":["Chemistry"]},{"key":"dc:creator","label":"Author","values":["Yen, Teh Fu"]}]},{"id":"academic_context","label":"Academic Context","entries":[{"key":"dc:date.accessioned","label":"Dc Date Accessioned","values":["2014-03-14T21:08:46Z"]},{"key":"dc:date.available","label":"Dc Date Available","values":["2014-03-14T21:08:46Z","2010-01-12"]},{"key":"dc:date.issued","label":"Date","values":["1955"]},{"key":"dc:publisher","label":"Institution","values":["Virginia Tech"]},{"key":"dc:type","label":"Dc Type","values":["Dissertation"]},{"key":"dc:type.dcmitype","label":"Dc Type Dcmitype","values":["Text"]},{"key":"thesis:degree_discipline","label":"Discipline","values":["Chemistry"]},{"key":"thesis:degree_level","label":"Degree Level","values":["doctoral"]},{"key":"thesis:degree_name","label":"Degree Name","values":["Ph. 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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."]},{"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":["Synthesis and properties of some 2,5-dihydrothiophene 1,1-dioxides"]}]}],"canonical_facts":{"dc:contributor.department":["Chemistry"],"dc:creator":["Yen, Teh Fu"],"dc:date.accessioned":["2014-03-14T21:08:46Z"],"dc:date.available":["2014-03-14T21:08:46Z","2010-01-12"],"dc:date.issued":["1955"],"dc:description.abstract":["1. 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."],"dc:description.degree":["Ph. D."],"dc:format.medium":["BTD"],"dc:format.mimetype":["application/pdf"],"dc:identifier.other":["etd-01122010-020235"],"dc:identifier.uri":["http://hdl.handle.net/10919/37189"],"dc:language.iso":["en"],"dc:publisher":["Virginia Tech"],"dc:rights":["In Copyright"],"dc:rights.uri":["http://rightsstatements.org/vocab/InC/1.0/"],"dc:title":["Synthesis and properties of some 2,5-dihydrothiophene 1,1-dioxides"],"dc:type":["Dissertation"],"dc:type.dcmitype":["Text"],"thesis:degree_discipline":["Chemistry"],"thesis:degree_level":["doctoral"],"thesis:degree_name":["Ph. D."],"thesis:institution_name":["Virginia Polytechnic Institute and State University"]},"updated_at":"2026-07-22T22:19:00Z"}