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1992 Fiscal Year Final Research Report Summary

Studies on Synthesis, Reaction and Functionality of the Bridged Aromatic Compounds

Research Project

Project/Area Number 02640399
Research Category

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

Allocation TypeSingle-year Grants
Research Field 有機化学一般
Research InstitutionSAGA UNIVERSITY

Principal Investigator

YAMATO Takehiko  Faculty of Science and Engineering Saga University Associate Professor, 理工学部, 助教授 (60136562)

Project Period (FY) 1990 – 1992
KeywordsBridged Aromatic Compounds / Cyclophanes / Strained Molecule / Aromaticity / Electrophilic Substitution / Macrocyclic Caged Compounds / Host-Guest Interaction / Molecular Material
Research Abstract

1. The development of synthesis of the bridged aromatic compounds Although there are numerous reports concerning synthesis of the bridged aromatic compounds, their preparative routes seem to be too long for practical purposes. The [2.2]meta- and [2.2]metaparacyclophanes are so highly strained compounds that may be reactive toward many reagents. However, the chemistry of these compounds is very limited since their preparation from easily available compounds are very limited. In this work, we have developed the convenient preparation of the strained bridged aromatic compounds using the tert-butyl function as a positional protecting group on aromatic ring. Furthermore, we have applied this method to the synthesis of large membered macrocyclic metacyclophanes.
2. Relationship between the reactivity and structures. Electrophilic substitution reactions of medium-sized cyclophanes were studied in order to investigate the relationship between the reactivity and the molecular strain. For example, in the electrophilic aromatic substitution of 8-substituted [2.2]metaparacyclophanes the isomerization and tramsannular reaction due to the release of the molecular strain were observed. We have studied on the reactive organic intermediates, which are contained cyclophane skeleton, for example, carbenes, nitrenes, and benzaynes etc.
3. The development to the advanced materials. The conformational studies of cyclophanes and the application for the advanced materials, for example photo-response materials, host compounds, and new conductive cyclophane polymers etc. were investigated. For example, the functionalized macrocyclic metacyclophanes, which we have designed in this work found to act as host compounds and have abilities of molecular recognition such as organic compounds and metal ions.
The relationship between the reactivity and physical properties was also investigated by X-ray diffraction analysis.

  • Research Products

    (66 results)

All Other

All Publications (66 results)

  • [Publications] Masashi Tashiro: "Metacyclophanes and Related Compounds.26.Tetrahydroxy[2.n.2.n]metacyclophanes.Preparation,Reaction,and Spectra." Journal of Organic Chemistry. 55. 2404-2409 (1990)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Takehiko Yamato: "A Cnovenient Preparation of 1,n-Bis(5-tert-butyl-2-substituted phenyl)alkanes" Chemistry Express. 5. 769-772 (1990)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Takehiko Yamato: "A Convenient Preparation OF[2.1.1]Metacyclophanes" Chemistry Express. 5. 773-776 (1990)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Takehiko Yamato: "Preparation of Novel Maclocyclic Compound,[2.2.0.2.2.0]Metacyclophane" Chemistry Express. 5. 777-780 (1990)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Takehiko Yamato: "A Convenient Preparation of 10,15-Dihydro-5H-tribenzo-[a,d,g]cyclononene Using Lewis Acids Catalyzed Cyclo-benzylation" Chemistry Express. 5. 941-944 (1990)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Akira Miyazawa: "A New Synthetic Route to 4-Alkylpyrenes from 2,7-Di-tert-butyl-trans-10b,10c-dimethyl-10b,10c-dihydropyrenes" Journal of Organic Chemistry. 56. 1334-1337 (1991)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Takehiko Yamato: "Solid Superacids Catalyzed Organic Synthesis 4.Perfluorinated Resinsulfonic Acid(Nafion-H)Catalyzed Benzylation of Benzene and Substituted Benzenes" Journal of Organic Chemistry. 56. 2089-2091 (1991)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Takehiko Yamato: "A Convenient Preparation of 1,2,3,6,8-pentamethyl-trans-10b,10c-dimethyl-10b,10c-dihydropyrene" Chemistry Express. 6. 285-288 (1991)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Takehiko Yamato: "Medium-Sized Cyclophanes.7.Bromination of[3.2]-metacyclophanes" Journal of Chemical Research(S),(M). (S)150-151 (M)1520-1531 (1991)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Takehiko Yamato: "Medium-Sized Cyclophanes.8.A New Preparative Route to 8,16-Disubstituted[2.2]metacyclophane-1-enes" Journal of Chemical Research(S). 152-153 (1991)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Takehiko Yamato: "Medium-Sized Cyclophanes.Part 9.Formation of trans-10b,10c-Dimethyl-10b,10c-dihydropyrenes in Bromination of anti-8,16-Dimethyl[2.2]metacyclophane-1-enes with Bromine" Journal of Chemical Research(S). 182-183 (1991)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Takehiko Yamato: "Medium-Sized Cyclophanes.Part 10.Conformations of 9-Substituted 2,11-Dithia[3.3]orthometacyclophanes" Journal of Chemical Research(S),(M). (S)274-275 (M)2567-2588 (1991)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Takehiko Yamato: "Medium-Sized Cyclophanes.11.Nitration of [n.2]Metacyclophanes" Chemistry Express. 6. 663-666 (1991)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Takehiko Yamato: "Organic Reactions Catalyzed by Solid Superacids.7.Perfluorinated Sulfonic Acid Resin(Nafion-H)Catalyzed Friedel-Crafts Cyclobenzylation of Benzene with Bis(hydroxymethyl)diarylalkanes" Journal of Chemical Research(S),(M). (S)242-243 (M)2414-2438 (1991)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Takehiko Yamato: "The Preparation of[2](2,6)-p-benzoquinono[2]-metacyclophane" Chemistry Express. 6. 347-350 (1991)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Masashi Tashiro: "Preparation of [2.1.4](1,2,3)Cyclophanes by Reaction of 2,8-Di-tert-butyl-4,6-bis(chloromethyl)dibenzo[a,d]cyclo-heptene with Aromatic Compounds in the Presence of TiCl_4" Journal of Chemical Research(S),(M). (S)94-95 (M)0834-0844 (1991)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Takehiko Yamato: "Medium-Sized Cyclophanes.Part 12.Reaction of 8,16-Mimethyl[2.2]metacyclophane with Iodine Monochloride.A Preparative Route to 2,7-Dichloro-trans-10b,10c-dimethyl-10b,10c-dihydropyrene" Journal of Chemical Research(S). 276-277 (1991)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Takehiko Yamato: "Medium-Sized Cyclophanes.Preparation and Valence Tauto-merism of 8,16-Disubstituted[2.2]metacyclophane-1,9-dienes." Journal of Organic Chemistry. 57. 266-270 (1992)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Takehiko Yamato: "Medium-Sized Cyclophanes.Bromination of 8-Methoxy-[2.2]metacyclophanes." Journal of Organic Chemistry. 57. 271-275 (1992)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Takehiko Yamato: "Medium-Sized Cyclophanes.Part 15.Bromination and Lewis Acids Catalyzed Isomerization of 8,16-Diethyl[2.2]meta-cyclophane." Journal of Organic Chemistry. 57. 365-366 (1992)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Takehiko Yamato: "Preparation and Conformational Properties of Tetra-hydroxy[3.1.3.1]metacyclophane" J.Chem.Soc.Chem.Commun.861-862 (1992)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Takehiko Yamato: "The Preparation and Novel[3.3]Sigmatropic Rearrangement of Cyclophanes Having a Spiro Skeleton" J.Chem.Soc.Chem.Commun.865-866 (1992)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Takehiko Yamato: "Medium-Sized Cyclophanes.17.Bromination of 8,16-Dihydroxy[2.2]metacyclophanes" Journal of Organic Chemistry. 57. 6368-6371 (1992)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Takehiko Yamato: "Medium-Sized Cyclophanes.Part 18.5-tert-Butyl-8-substituted[2.2]metaparacyclophanes:Preparation,X-ray Diffraction Studies,and their Treatment with Lewis Acids in Benzene" J.Chem.Soc.Perkin Trans.1. 2675-2682 (1992)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Takehiko Yamato: "Medium-Sized Cyclophanes.19.Preparation and Conformational Studies of [m.n]Metacyclophanes" Journal of Organic Chemistry. 57. 5243-5246 (1992)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Takehiko Yamato: "Medium-Sized Cyclophanes,20.Synthesis and Conformational Studies of syn-and anti-Dihydroxy[n.2]metacyclophanes" Chem.Ber.125. 2443-2454 (1992)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Takehiko Yamato: "Medium-sized Cyclophanes.21.Preparation and Reduction of syn-and anti-[3.2]metacyclophanequinone and anti-[4.2]-metacyclophanequinone" Journal of Organic Chemistry. 57. 5154-5158 (1992)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Takehiko Yamato: "Medium-sized Cyclophanes.Part.23.Iodine-induced Cycloisomerization Reaction of 8-Methyl[2.2]metacyclo-phanes to 3a-Methyl-1,2,3,3a,4,5-hexahydropyrenes" Journal of Chemical Research(S). 420-421 (1992)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Takehiko Yamato: "Medium-Sized Cyclophanes.24.Bromination of 8-Substituted[2.2]Metaparacyclophanes" Journal of Organic Chemistry. 57. 6969-6972 (1992)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Takehiko Yamato: "Medium-Sized Cyclophanes.Part 17.Formylation of [n.2]Metacyclophanes" Journal of Chemical Research(S). 44-45 (1993)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Takehiko Yamato: "Medium-Sized Cyclophanes.Part 25.Bromination and Reactions of[2.n]Metacyclophan-1-enes and Isolaton of Two Isomers of 1-Bromo[2.n]metacyclophanes" Chem.Ber.

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Takehiko Yamato: "Medium-Sized Cyclophanes.Part 26.Electrophilic Substitution of[2.2.2](1,2,3)Cyclophanes" Journal of Chemical Research.

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Takehiko Yamato: "Novel Spherand-type Calixarenes-Synthesis,Conformational Studies,and Isomer Separation" Chem.Ber.

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] M. Tashiro: "Metacyclophanes and Related Compounds. 26. Tetrahydroxy[2.n.2.n.]metacyclophanes. Preparation, Reaction, and Spectra." J. Org. Chem.55. 2404-2409 (1990)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] T. Yamato: "A Convenient Preparation of 1,n-Bis(5-tert-butyl-2-substituted phenyl)alkanes" Chemistry Express. 5. 769-772 (1990)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] T. Yamato: "A Convenient Preparation of [2.1.1]Metacyclophanes" Chemistry Express. 5. 773-776 (1990)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] T. Yamato: "Preparation of Novel Maclocyclic Compound, [2.2.0.2.2.0]Metacyclophane" Chemistry Express. 5. 777-780 (1990)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] T. Yamato: "A Convenient Preparation of 10,15-Dihydro-5H-tribenzo[a,d,g]cyclononene Using Lewis Acids Catalyzed Cyclobenzylation" Chemistry Express. 5. 941-944 (1990)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] A. Miyazawa: "A New Synthetic Route to 4-Alkylpyrenes from 2,7-Di-tert-butyl-trans-10b,10c-dimethyl-10b,10c-dihydropyrenes" J. Org. Chem.56. 1334-1337 (1991)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] T. Yamato: "Solid Superacids Catalyzed Organic Synthesis 4. Perfluorinated Resinsulfonic Acid (Nafion-H) Cat alyzed Benzylation of Benzene and Substituted Benzenes" J. Org. Chem.56. 2089-2091 (1991)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] T. Yamato: "A Convenient Preparation of 1,2,3,6,8- pentamethyl-trans-10b,10c-dimethyl-10b,10c- dihydropyrene" Chemistry Express. 6. 285-288 (1991)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] T. Yamato: "Medium-Sized Cyclophanes. 7. Bromination of [3.2]metacyclophanes" J. Chem. Research. (S), (M). 150-151 1520-1531 (1991)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] T. Yamato: "Medium-Sized Cyclophanes. 8. A New Preparative Route to 8,16-Disubstituted [2.2]metacyclophan-1-enes" J. Chem. Research. (S). 152-153 (1991)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] T. Yamato: "Medium-Sized Cyclophanes. Part 9. Formation of trans-10b,10c-Dimethyl-10b,10c-dihydropyrenes in Bromination of anti-8,16-Dimethyl[2.2]metacyclo-phane-1-enes with Bromine" J. Chem. Research. (S). 182-183 (1991)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] T. Yamato: "Medium-Sized Cyclophanes. Part 10. Conformations of 9-Substituted 2,11-Dithia[3.3]orthometacyclo-phanes" J. Chem. Research. (S), (M). 274-275 2567-2588 (19911991)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] T. Yamato: "Medium-Sized Cyclophanes. 11. Nitration of [n.2]Metacyclophanes" Chemistry Express. 6. 663-666 (1991)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] T. Yamato: "Organic Reactions Catalyzed by Solid Superacids. 7. Perfluorinated Sulfonic Acid Resin (Nafion-H) Catalyzed Friedel-Crafts Cyclobenzylation of Benzene with Bis(hydroxymethyl)diarylalkanes" J. Chem. Research. (S), (M). 242-243 2414-2438 (1991)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] T. Yamato: "The Preparation of [2](2,6)-p-benzoquinono[2]-metacyclophane" Chemistry. Express. 6. 347-350 (1991)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] M. Tashiro: "Preparation of [2.1.4](1,2,3)Cyclophanes by Reaction of 2,8-Di-tert-butyl-4,6-bis-(chloromethyl)dibenzo[a,d]cycloheptene with Aromatic Compounds in the Presence of TiCl_4" J. Chem. Research. (S), (M). 94-95 0834-0844 (1991)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] T. Yamato: "Medium-Sized Cyclophanes. Part 12. Medium-Sized Cyclophanes. Part 12. Reaction of 8,16-Dimethyl-[2.2]metacyclophane with Iodine Monochloride. A Preparative Route to 2,7-Dichloro-trans-10b,10c-dimethyl-10b,10c-dihydropyrene" J. Chem. Research. (S). 276-277 (1991)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] T. Yamato: "Medium-Sized Cyclophanes. Preparation and Valence Tautomerism of 8,16-Disubstituted [2.2]metacyclo-phan-1,9-dienes" J. Org. Chem.57. 266-270 (1991)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] T. Yamato: "Medium-Sized Cyclophanes. Bromination of 8-Methoxy[2.2]metacyclophanes" J. Org Chem.57. 271-275 (1992)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] T. Yamato: "Medium-Sized Cyclophanes. Part 15. Bromination and Lewis Acids Catalyzed Isomerization of 8,16-Diethyl[2.2]metacyclophane" J. Org. Chem.57. 365-366 (1992)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] T. Yamato: "Preparation and Conformational Properties of Tetrahydroxy[3.1.3.1]metacyclophane" J. Chem. Soc. Chem. Commun.861-862 (1991)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] T. Yamato: "The Preparation and Novel [3.3]Sigmatropic Rearrangement of Cyclophanes Having a Spiro Skeleton" J. Chem. Soc. chem. Commun.865-866 (1992)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] T. Yamato: "Medium-Sized Cyclophanes. 17. Bromination of 8,16-Dihydroxy[2.2]metacyclophanes" J. Org. Chem.57. 6368-6371 (1992)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] T. Yamato: "Medium-Sized Cyclophanes. Part 18.5-tert-Butyl-8-substituted [2.2]metaparacyclophanes: Preparation, X-ray Diffraction Studies, and their Treatment with Lewis Acids in Benzene" J. Chem. Soc. Perkin Trans. 1. 2675-2682 (1992)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] T. Yamato: "Medium-Sized Cyclophanes. 19. Preparation and Conformational Studies of [m.n]Metacyclophanes" J. Org. Chem.57. 5243-5246 (1992)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] T. Yamato: "Medium-Sized Cyclophanes, 20. Synthesis and Conformational Studies of syn- and anti- Dihydroxy[n.2]metacyclophanes" Chem. Ber.125. 2443-2454 (1992)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] T. Yamato: "Medium-sized Cyclophanes. 21. Preparation and Reduction of syn- and anti-[3.2]metacyclophanequinone and anti-[4.2]metacyclophane-quinone" J. Org. Chem.57. 5154-5158 (1992)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] T. Yamato: "Medium-sized Cyclophanes. Part. 23. Iodine-induced Cycloisomerization Reaction of 8-Methyl[2.2]metacyclophanes to 3a-Methyl-1,2,3,3a,4,5-hexahydropyrenes" J. Chem. Research. (S). 420-421 (1992)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] T. Yamato: "Medium-Sized Cyclophanes. 24. Bromination of 8-Substituted [2.2]Metaparacyclophanes" J. Org. Chem.57. 6969-6972 (1992)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] T. Yamato: "Medium-Sized Cyclophanes. Part 17. Formylation of [n.2]Metacyclophanes" J. Chem. Research. (S). 44-45 (1993)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] T. Yamato: "Medium-Sized Cyclophanes. Part 25. Bromination and Reactions of [2.n]Metacyclophan-1-enes and Isolaton of Two Isomers of 1-Bromo[2.n]meta-cyclophanes" Chem. Ber.

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] T. Yamato: "Medium-Sized Cyclophanes. Part 26. Electrophilic Substitution of [2.2.2](1,2,3)Cyclophanes" J. Chem. Research. (S).

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] T. Yamato: "Novel Spherand-type Calixarenes - Synthesis, Conformational Studies, and Isomer Separation" Chem. Ber.

    • Description
      「研究成果報告書概要(欧文)」より

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Published: 1994-03-24  

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