{"id":{"repo_id":"wku-diss","oai_identifier":"oai:digitalcommons.wku.edu:theses-1024"},"canonical_url":"https://search.dev.ndltd.org/etd/wku-diss/oai:digitalcommons.wku.edu:theses-1024","repository":{"repo_id":"wku-diss","name":"Western Kentucky University","base_url":"https://digitalcommons.wku.edu/do/oai/"},"display":{"title":"Proposed Route to Cyclopenta[c]thiophenes via Activated Methylene","abstract":"The synthesis of cyclopenta[c]thiophenes has been sparsely reported in the literature owing to several difficulties involved in their synthesis. The present work involves the proposed synthesis of cyclopenta[c]thiophenes and their precursors using activated methylene. Cyclopenta[c]thiophene compounds show promise in the field of polymer and catalysis chemistry. These substituted polythiophenes are potential organic semiconductors and anti-tumor agents. The research presented shows the successful and novel conversion of 3,4-bis(chloromethyl)-2,5-dimethylthiophene and 3,4-bis(bromomethyl)-2,5-dimethylthiophene to a fused 5,5'-fused membered ring which is the precursor to cyclopenta[c]thiophene the sulfone ester, 5-carbomethoxy-5- phenylsulfonyl-1,3-dimethyl-5,6-dihydro-4H-cyclopenta[c]thiophene, in just two steps as compared to four steps previously reported in the literature. This valuable precursor intermediate currently made and proven by characterization is one synthetic step away from a substituted cyclopenta[c]thiophene. A paper has been submitted to <i>Letters in Organic Chemistry</i> to report our work.","abstract_html":"The synthesis of cyclopenta[c]thiophenes has been sparsely reported in the literature owing to several difficulties involved in their synthesis. The present work involves the proposed synthesis of cyclopenta[c]thiophenes and their precursors using activated methylene. Cyclopenta[c]thiophene compounds show promise in the field of polymer and catalysis chemistry. These substituted polythiophenes are potential organic semiconductors and anti-tumor agents. The research presented shows the successful and novel conversion of 3,4-bis(chloromethyl)-2,5-dimethylthiophene and 3,4-bis(bromomethyl)-2,5-dimethylthiophene to a fused 5,5&#x27;-fused membered ring which is the precursor to cyclopenta[c]thiophene the sulfone ester, 5-carbomethoxy-5- phenylsulfonyl-1,3-dimethyl-5,6-dihydro-4H-cyclopenta[c]thiophene, in just two steps as compared to four steps previously reported in the literature. This valuable precursor intermediate currently made and proven by characterization is one synthetic step away from a substituted cyclopenta[c]thiophene. A paper has been submitted to &lt;i&gt;Letters in Organic Chemistry&lt;/i&gt; to report our work.","abstract_has_math":false,"creators":["Karambelkar, Vineet V"],"institution":null,"degree_name":"Master of Science","degree_level":null,"degree_discipline":"Department of Chemistry","degree_department":null,"school":null,"contributors":["Dr. Chad A. Snyder, Dr. Cathleen J. Webb, Dr. Rui Zhang"],"advisors":[],"committee_chairs":[],"committee_members":[],"year":2008,"date_issued":"2008-08-01T07:00:00Z","date_published":"2008-08-01T07:00:00Z","updated_at":"2026-07-24T06:07:03Z","subjects":["polymer chemistry","catalysis chemistry","anti-tumor agents","organic semiconductors","Chemistry","Organic Chemistry"],"languages":[],"rights":[],"rights_urls":[],"identifier_entries":[]},"links":{"outbound_url":"https://digitalcommons.wku.edu/theses/25","outbound_label":"Repository record","outbound_source":"dc:identifier"},"metadata_groups":[{"id":"people","label":"People","entries":[{"key":"dc:contributor","label":"Contributor","values":["Dr. Chad A. Snyder, Dr. Cathleen J. Webb, Dr. Rui Zhang"]},{"key":"dc:creator","label":"Author","values":["Karambelkar, Vineet V"]}]},{"id":"academic_context","label":"Academic Context","entries":[{"key":"dc:type","label":"Dc Type","values":["Thesis"]},{"key":"thesis:degree_discipline","label":"Discipline","values":["Department of Chemistry"]},{"key":"thesis:degree_name","label":"Degree Name","values":["Master of Science"]}]},{"id":"subjects_keywords","label":"Subjects and Keywords","entries":[{"key":"dc:subject","label":"Dc Subject","values":["polymer chemistry","catalysis chemistry","anti-tumor agents","organic semiconductors","Chemistry","Organic Chemistry"]}]},{"id":"identifiers","label":"Identifiers","entries":[{"key":"dc:identifier","label":"Identifier","values":["https://digitalcommons.wku.edu/theses/25"]}]},{"id":"additional","label":"Additional Metadata","entries":[{"key":"dc:description.abstract","label":"Abstract","values":["The synthesis of cyclopenta[c]thiophenes has been sparsely reported in the literature owing to several difficulties involved in their synthesis. The present work involves the proposed synthesis of cyclopenta[c]thiophenes and their precursors using activated methylene. Cyclopenta[c]thiophene compounds show promise in the field of polymer and catalysis chemistry. These substituted polythiophenes are potential organic semiconductors and anti-tumor agents. The research presented shows the successful and novel conversion of 3,4-bis(chloromethyl)-2,5-dimethylthiophene and 3,4-bis(bromomethyl)-2,5-dimethylthiophene to a fused 5,5'-fused membered ring which is the precursor to cyclopenta[c]thiophene the sulfone ester, 5-carbomethoxy-5- phenylsulfonyl-1,3-dimethyl-5,6-dihydro-4H-cyclopenta[c]thiophene, in just two steps as compared to four steps previously reported in the literature. This valuable precursor intermediate currently made and proven by characterization is one synthetic step away from a substituted cyclopenta[c]thiophene. A paper has been submitted to <i>Letters in Organic Chemistry</i> to report our work."]},{"key":"dc:title","label":"Title","values":["Proposed Route to Cyclopenta[c]thiophenes via Activated Methylene"]}]}],"canonical_facts":{"dc:contributor":["Dr. Chad A. Snyder, Dr. Cathleen J. Webb, Dr. Rui Zhang"],"dc:creator":["Karambelkar, Vineet V"],"dc:description.abstract":["The synthesis of cyclopenta[c]thiophenes has been sparsely reported in the literature owing to several difficulties involved in their synthesis. The present work involves the proposed synthesis of cyclopenta[c]thiophenes and their precursors using activated methylene. Cyclopenta[c]thiophene compounds show promise in the field of polymer and catalysis chemistry. These substituted polythiophenes are potential organic semiconductors and anti-tumor agents. The research presented shows the successful and novel conversion of 3,4-bis(chloromethyl)-2,5-dimethylthiophene and 3,4-bis(bromomethyl)-2,5-dimethylthiophene to a fused 5,5'-fused membered ring which is the precursor to cyclopenta[c]thiophene the sulfone ester, 5-carbomethoxy-5- phenylsulfonyl-1,3-dimethyl-5,6-dihydro-4H-cyclopenta[c]thiophene, in just two steps as compared to four steps previously reported in the literature. This valuable precursor intermediate currently made and proven by characterization is one synthetic step away from a substituted cyclopenta[c]thiophene. A paper has been submitted to <i>Letters in Organic Chemistry</i> to report our work."],"dc:identifier":["https://digitalcommons.wku.edu/theses/25"],"dc:subject":["polymer chemistry","catalysis chemistry","anti-tumor agents","organic semiconductors","Chemistry","Organic Chemistry"],"dc:title":["Proposed Route to Cyclopenta[c]thiophenes via Activated Methylene"],"dc:type":["Thesis"],"thesis:degree_discipline":["Department of Chemistry"],"thesis:degree_name":["Master of Science"]},"updated_at":"2026-07-24T06:07:03Z"}