Advisor(s) - Committee Chair
Dr. Chad A. Snyder, Dr. Cathleen J. Webb, Dr. Rui Zhang
Department of Chemistry
Master of Science
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 Letters in Organic Chemistry to report our work.
Chemistry | Organic Chemistry | Polymer Chemistry
Karambelkar, Vineet V., "Proposed Route to Cyclopenta[c]thiophenes via Activated Methylene" (2008). Masters Theses & Specialist Projects. Paper 25.