Syntheses and Reactions of Condensed Polycyclic Aromatic Hydrocarbons Having Five-membered Ring
| Project/Area Number |
02640381
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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 |
有機化学一般
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| Research Institution | Utsunomiya University |
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Principal Investigator |
MINABE Masahiro Utsunomiya University, Fac. Engineering, Professor, 工学部, 教授 (40007993)
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| Co-Investigator(Kenkyū-buntansha) |
KIMURA Takao Utsunomiya University, Fac. Engineering, Assistant, 工学部, 助手 (10114159)
TSUBOTA Motohiro Utsunomiya University, Fac. Engineering, Ass. professor, 工学部, 助教授 (10007974)
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| Project Period (FY) |
1990 – 1991
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| Project Status |
Completed (Fiscal Year 1991)
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| Budget Amount *help |
¥500,000 (Direct Cost: ¥500,000)
Fiscal Year 1991: ¥500,000 (Direct Cost: ¥500,000)
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| Keywords | condensed polycyclic aromatic hydrocarbon / synthesis / NMR spectra / electrophilic substitution / cationic polymerization / catalytic hydrogenation / reversed phase HPLC column / cyclic oligomer / イタコン酸ジメチル / 縮合多環芳香族化合物 / インデノ〔1,2,3ーcd〕ピレン / シクロペンタ〔cd〕ピレン / ポリアミド樹脂 / 1,4ービス〔9ーフルオレニル)ー14ーミクロヘキサンジオ-ル |
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| Research Abstract |
1.3-Ethyl-, 5-ethyl-, and 4- tert-butyl-12-ethylindeno[1, 2, 3- cd]pyrene are synthesized and their NMR spectra were characterized. Chemical shift of NMR spectrum of a polycondensed aromatic hydrocarbon is suggested to be estimated by the combination of chemical shift of the parent hydrocarbon and that of substituted naphthalenes.
2. Reaction of cyclopenta[cd]pyrene with electrophiles takes place a cationic polymerization giving polymer attached with electrophile. 3, 4-Dihydrocyclopentapyiene and cyclopentapyiene-3(4 H)-one gave mainly 8-, 6-, and I-substituted compounds by the electrophilic substitution ; these findings are compared with the reactivities of monosubstituted pyrenes.
3. Catalytic hydrogenation of fluorene, phenanthrene, fluoianthene, pylene, and 4H-cyclopenta[def]phenanthrene in the presence of Raney nickel were examined and discussed in terms of reactivities and of adsorption properties. For example, fluorene is poorly adsorbed on catalyst and hydrogenation of fluorene is slow in the presence of an other hydrocarbon.
4. Liquid phase for reversed phase chromatography was obtained by linking of silicagel and benzyl, cyano, or benzyloxycarbonyl group with decamethylene bridge, in order to produced high selective column for partially hydrogenated polycondensed hydrocarbons. The characterization of the column was determined in comparison with commercially-available column.
5. Telomerization of dimethyl itaconate was compared with that of methyl metacrylate. Cyclic oligomers, ones of dimeric adducts were isolated ; the formation sequence and the reactivities of these oligomers are discussed.
6. Fluorenylidene compounds could not obtained by the dehydration of 1, 4-bis(9-fluorenly)-1, 4-cyclohexanedio. Treatment of 2-(3-fluoranthenyl) cyclohexanone with PPA gave mainly intermolecular dehydration products, but not intramolecular indenofluoranthene. Synthesis of cyclohepta [l] cyclopenta [def] phenanthrene is failed at present.
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Report
(3 results)
Research Products
(20 results)
