Proposed Route to Cyclopenta[c]thiophenes via Activated Methylene

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.

Name thesis:degree_name

Master of Science

Discipline thesis:degree_discipline

Department of Chemistry

Year

2008

Author dc:creator

• Karambelkar, Vineet V

Contributors dc:contributor

• Dr. Chad A. Snyder, Dr. Cathleen J. Webb, Dr. Rui Zhang

• polymer chemistry
• catalysis chemistry
• anti-tumor agents
• organic semiconductors
• Chemistry
• Organic Chemistry

Repository record dc:identifier

https://digitalcommons.wku.edu/theses/25

OAI identifier oai:identifier

oai:digitalcommons.wku.edu:theses-1024