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Syntheses and Reactions of Condensed Polycyclic Aromatic Hydrocarbons Having Five-membered Ring

Research Project

Project/Area Number 02640381
Research Category

Grant-in-Aid for General Scientific Research (C)

Allocation TypeSingle-year Grants
Research Field 有機化学一般
Research InstitutionUtsunomiya University

Principal Investigator

MINABE Masahiro  Utsunomiya University, Fac. Engineering, Professor, 工学部, 教授 (40007993)

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)
Project Period (FY) 1990 – 1991
Project Status Completed (Fiscal Year 1991)
Budget Amount *help
¥500,000 (Direct Cost: ¥500,000)
Fiscal Year 1991: ¥500,000 (Direct Cost: ¥500,000)
Keywordscondensed 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
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.

Report

(3 results)
  • 1991 Annual Research Report   Final Research Report Summary
  • 1990 Annual Research Report
  • Research Products

    (20 results)

All Other

All Publications (20 results)

  • [Publications] Masahiro Minabe et al.: "Electrophilic substitution of polycyclic fluoranthene hydrocarbons" J.Am.Chem.Soc.111. 3809-3812 (1989)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1991 Final Research Report Summary
  • [Publications] Masahiro Minabe,Norio Shibuya: "Nitration of indeno〔1,2,3-cd〕pyrene and mutagenic activities of related compounds" Chem.Res.Toxicology. 2. 357-358 (1989)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1991 Final Research Report Summary
  • [Publications] Masahiro Minabe et al.: "Synthesis of some ethylindeno〔1,2,3-cd〕pyrene" J.Org.Chem.57. 1012-1015 (1992)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1991 Final Research Report Summary
  • [Publications] Masahiro Minabe et al.: "Reactivities of cyclopenta〔cd〕pyrene derivatives with electrophiles" J.Org.Chem.

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1991 Final Research Report Summary
  • [Publications] Masahiro Minabe,Norio Shibuya: "Mutagenic activities of nitration products of cyclopenta〔cd〕pyrene and its homologs" Chem.Res.Toxicology.

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1991 Final Research Report Summary
  • [Publications] Masahiro Minabe et al.: "Realtive reactivities of polycyclic aromatic hydrocarbons under catalytic hydrogenation with Raney nickel" Bull.Chem.Soc.Jpn.

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1991 Final Research Report Summary
  • [Publications] Masahiro Minabe, Bongsup P. Cho, and Ronald G. Harvey: "Electrophilic substitution of polycyclic fluoranthene hydrocarbons" J. Am. Chem. Soc.111 (No. 11). 3809-3812 (1989)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1991 Final Research Report Summary
  • [Publications] Masahiro Minabe and Norio Shibuya: "Nitration of indeno [1, 2, 3, -cd] pyrene and mutagenic activities of related compounds" Chem. Res. Toxicol.2 (No. 6). 357-358 (1989)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1991 Final Research Report Summary
  • [Publications] Masahiro Minabe, Motohiko Ishida, Takao Kimura Motohiro Tsubota, and Masaaki Yoshida: "Synthesis of some ethylindeno [1, 2, 3, - cd] pyrene" J. Org. Chem.57 (No. 3). 1012-1015 (1992)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1991 Final Research Report Summary
  • [Publications] Masahiro Minabe, Ryuuji Nishimura, Takao Kimura, and Motochiro Tsubota: "Reactivities of cyclopental [cd] pyrene derivatives with electrophiles" J. Org. Chem.

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1991 Final Research Report Summary
  • [Publications] Masahiro Minabe and Norio Shibuya: "Mutagenic activities of nitration products of cyclopenta [cd] pyrene and its homologs" Chem. Res. Toxicol.

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1991 Final Research Report Summary
  • [Publications] Masahiro Minabe, Fumihiko Mishina, Takao Kimura, and Motohiro Tsubota: "Relative reactivities of polycyclic aromatic hydrocarbons under catalytic hydrogenation with Raney nickel." Bull. Chem. soc. Jpn.

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1991 Final Research Report Summary
  • [Publications] Masahiro Minabe et al: "Synthesis of some ethylindeno[1,2,3ーcd]pyrene" J.Org.Chem.57. 1012-1015 (1992)

    • Related Report
      1991 Annual Research Report
  • [Publications] Masahiro Minabe et al: "Reactivities of cyclopenta[cd]pyrene derivatives with electrophiles" J.Org.Chem.

    • Related Report
      1991 Annual Research Report
  • [Publications] Masahiro Minabe: "Mutagenic activities of nitration products of cyclopenta[cd]pyrene and its homologs" Chem.Res.Toxicol.

    • Related Report
      1991 Annual Research Report
  • [Publications] Masahiro Minabe et al: "Relative reactivities of polycyclic aromatic hydrocarbons under catalytic hydrogenation with Raney nickel" Bull.Chem.Soc.Jpn.

    • Related Report
      1991 Annual Research Report
  • [Publications] Takao Kimura: "Synthesis and characterization of polyamide by interfacial polycondensation of dichloroformylーcontaining αーlactone with hexamethylene diamine" Polymer Journal. 22. 1015-1021 (1990)

    • Related Report
      1990 Annual Research Report
  • [Publications] Masahiro Minabe: "Syntheses of 3ー,5ー,and 12ーethylindeno[1,2,3ーcd]pyrenes" J.Org.Chem.

    • Related Report
      1990 Annual Research Report
  • [Publications] Masahiro Minabe: "Catalytic hydrogenation of some polycyclic aromatic hydrocarbons" Bull.Chem.Soc.Jpn.

    • Related Report
      1990 Annual Research Report
  • [Publications] Masahiro Minabe: "Reactivities of cyclopenta[cd]phrene derivatives" J.Org.Chem.

    • Related Report
      1990 Annual Research Report

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Published: 1991-04-01   Modified: 2016-04-21  

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