A Modified Route to Cyclopenta[C]Thophenes Via Grignard Reagents

The synthesis of cyclopenta[c]thiophenes is sparsely found in literature due to the several difficulties of their synthesis. Our research has shown that we could modify a previously known route to 1,3-disubstituted cyclopenta[c]thiophenes using traditional Grignard chemistry. Along the way we discovered the synthetic route we were using had several omissions. Therefore, we were required to completely fill in missing experimentals in order to obtain each cyclopenta[c]thiophene intermediate, in high purity and good yield. In addition, we were able to fully characterize via NMR, our intermediates which was found in the literature. Finally, we were able to show using 'H 13 and 13C NMR spectroscopy evidence of 5-alkyl-l,3-disubstituted cyclopenta[c]thiophenes by treating l,3-dimethyl-5,6-dihydro-4H-cyclopenta[c]thio-phene-5-one with an alkyl Grignard reagent. 1 A ser1i3e s of cyclopenta[c]thiophene intermediates will be presented along with their H and C NMR spectra. A discussion of cyclopenta[c]thiophene synthesis will be provided along with attempts to improve its experimental conditions. A paper has been submitted to Letters in Organic Chemistry to report our work.

Name thesis:degree_name

Master of Chemistry

Discipline thesis:degree_discipline

Department of Chemistry

Year

2007

Author dc:creator

• Bell, Amber

• Chemistry

Repository record dc:identifier

https://digitalcommons.wku.edu/theses/963

OAI identifier oai:identifier

oai:digitalcommons.wku.edu:theses-1966