MATSUI Masaki Gifu University, Faculty of Engineering, Assistant, 工学部, 助手 (60108058)
SHIBATA Katsuyoshi Gifu University, Faculty of Engineering, Assistant Professor, 工学部, 助教授 (80021591)
|Budget Amount *help
¥1,600,000 (Direct Cost : ¥1,600,000)
Fiscal Year 1990 : ¥400,000 (Direct Cost : ¥400,000)
Fiscal Year 1989 : ¥1,200,000 (Direct Cost : ¥1,200,000)
1. Fluorination of 2-carboxylic acids of heteroaromatics, such as furan, thiophene and N-methylpyrrole, by sulfur tetrafluoride were attempted to give only, tarry polymeric materials. 2,5-Dicarboxylic acids of furan and thiophene, however, afforded 2,5-bis (trifluoromethyl) furan and thiophene together with 5-trifluoromethy1-2-carboxylic acids of the corresponding heteroaromatics by fluorination with sulfur tetrafluoride. 2-Trifluoromethylfuran and thiophene were synthesized by decarboxylation of the 2-trifluoromethyl-5-carboxylic acids on heating in the presence of copper powder.
2. The lithiated furans and thiophenes containing trifluoromethyl groups were treated with 1,1-dichloro-2,2-difluoroethylene to give the corresponding furans and thiophenes with a 1-fluoro-2,2-dichlorovinyl group, which was then converted to a ethynyl group by dehalogenation with n-butyllithium.
3. Several trifluoromethyl-substituted furans and thiophenes with a ethynyl group were polymerized using a catalyst such as WC1_6-Ph_4Sn, to yield the corresponding polyacetylenes. 2,5-Bis (trifluoromethyl)-3-ethynylfuran and thiophene were found to give a high molecular weight polyacetylenes.