1990 Fiscal Year Final Research Report Summary
Syntheses of Acetylenes Substituted with Heteroaromatic Containing Trifluoromethyl Groups
| Project/Area Number |
01550645
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| Research Category |
Grant-in-Aid for General Scientific Research (C)
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| Allocation Type | Single-year Grants |
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| Research Field |
有機工業化学
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| Research Institution | Gifu University |
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Principal Investigator |
MURAMATSU Hiroshige Gifu University, Faculty of Engineering, Professor, 工学部, 教授 (20210065)
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| Co-Investigator(Kenkyū-buntansha) |
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)
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| Project Period (FY) |
1989 – 1990
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| Keywords | Trifluoromethyl Group / Furan Derivatives / Thiophene Derivatives / Heteroaromaticacetylene / Polyacetylene / Transition Metal Catalyst |
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| Research Abstract |
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.
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