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1992 Fiscal Year Final Research Report Summary

Participation of di- and tri-cations in Friedel-Crafts reactions.

Research Project

Project/Area Number 03453154
Research Category

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

Allocation TypeSingle-year Grants
Research Field Chemical pharmacy
Research InstitutionUniversity of Tokyo

Principal Investigator

SHUDO Koichi  Univ Tokyo Prof., 薬学部, 教授 (50012612)

Co-Investigator(Kenkyū-buntansha) OHWADA Tomo  Univ. Tokyo Assist. Prof., 薬学部, 助手 (20177025)
ENDO Yasuyki  Univ Tokyo Assoc. Prof., 薬学部, 助教授 (80126002)
Project Period (FY) 1991 – 1992
KeywordsFriedel-Crafts reaction / Iminiumbenzenium ion / Carbenium ion / Super acid / Trifluoromethanesulfonic acid / Gattermannreaction / Gattermann-Koch reaction
Research Abstract

Researches on di-and tri- cationic species as electrophiles in the reaction of benzene were performed. Dications and Trications propoded in the work are:
1.Iminium-benzenium dications
2.Diphenylmethylcations bearing a protonated carboxylic acid.
3.Diprotonated nitrostyrenes and nitroethylenes.
4.N,N-Diprotonated cinnamaldimines.
5.O,O-diprotonated cinnamaldehydes.
6.Diprotonated cyanides
7.triprotonated nitroacetic acid and their esters.
8.Diprotonated ketones.
9.Protnated acyl cations.
These novel species can be prepared in a strong acid and readily react with benzene. These results generalized the participation of di- or tricationic species in electrophilic aromatic substitution of benzene.

  • Research Products

    (12 results)

All Other

All Publications (12 results)

  • [Publications] T.Ohwada et al: "Friedel-crafts type reactions invelving di- and tricctionic species" J.Am.Chem.Soc. 113. 1364-1373 (1991)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] M.Yato et al: "Requirements for Houben-Hoesch and Gatlermann reactions." J.Am.Chem.Soc. 113. 691-692 (1991)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] Y.Endo et al: "Anionic 3,4-diaza[3,3] sigmatropic nearranglments of N,N'-diacylhydrazines" Tetruhedrom Letlers. 32. 4517-4520 (1992)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] N.Haga et al: "Acid-cataly 2ed Amino-migration of O-phenglhydroxylamines." J.Am.Chem.Soc. 114. 9795-9806 (1992)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] N.Haga et al: "Orbital Distortion in dibenzo bycyclo [2.2.2] octatrienes" Chem Pharm Bull. 40. 3349-3351 (1992)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] T.Ohwada: "Orbital Distortion arising from remoti substityents" J.Am.Chem.Soc. 114. 8815-8827 (1992)

    • Description
      「研究成果報告書概要(和文)」より
  • [Publications] T.Ohwada et al: "Friedel Crafts type reactions involving di-and tricationic species" J.Am.Chem.Soc.113. 1364-1373 (1991)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] M.Yato et al: "Requirment for Houben-Hoesh and Gattermann reactions" J. Am. Chem. Soc.113. 691-692 (1991)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] Y.Endo et al: "Anionic 3,4-diaza[3.3]rearrangement of N.N-diphenylhydrazines-" Tetrahedron Letters. 32. 4517-4520 (1992)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] N.Haga et al: "Acid-catalyzed amino-migration of O-phylhydroxylamines" J.Am.Chem. Soc.114. 9795-9806 (1992)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] N.Haga et al: "Orbital distortion in dibenzobicyclo[2.2.2.]octatrienes" Chem. Pharm. Bull.40. 3349-3351 (1992)

    • Description
      「研究成果報告書概要(欧文)」より
  • [Publications] T.Ohwada: "Orbital distrotion arising from remote substituents" J. Am.Chem. Soc.114. 8818-8827 (1992)

    • 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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