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Superelectrophilic Dications

Research Project

Project/Area Number 08457581
Research Category

Grant-in-Aid for Scientific Research (B)

Allocation TypeSingle-year Grants
Section一般
Research Field Chemical pharmacy
Research InstitutionGraduate School of Pharmaceutical Sciences, The University of Tokyo

Principal Investigator

SHUDO Koichi  The University of Tokyo, Graduate School of Pharmaceutical Sciences, Professor, 大学院・薬学系研究科, 教授 (50012612)

Co-Investigator(Kenkyū-buntansha) OHWADA Tomohiko  The University of Tokyo, Graduate School of Pharmaceutical Science, Assistant Pr, 大学院・薬学系研究科, 助手 (20177025)
Project Period (FY) 1996 – 1997
Project Status Completed (Fiscal Year 1997)
Budget Amount *help
¥7,600,000 (Direct Cost: ¥7,600,000)
Fiscal Year 1997: ¥2,200,000 (Direct Cost: ¥2,200,000)
Fiscal Year 1996: ¥5,400,000 (Direct Cost: ¥5,400,000)
KeywordsSuperelectrophiles / Dications / Friedel-Crafts Reactions / スーパーホ電子体 / NaZaruタイプ環化反応 / ケトン / フルオレン / フリーデル・クラフト反応 / 強酸 / ベンゼン
Research Abstract

Friedel-Crafts reactions are those involving electrophilic reactions of carbon electrophiles with aromatic compounds. Cationic intermediated, i. e., carbenium ions, have been proposed as electrophiles in these reactions. A great number of cationic species have been identified, some of which bear two positive charges. In spite of the elucidation of the structures of cationic species, there have been few studies on the electrophilic reactivity toward benzenes. Therefore even though the cationic species is detected, there are no systematic criteria to determine whether such a cation can act as an electrophile in Friedel-Crafts reactions. Here the structures and electrophilic reactivities of carbocations will be discussed, in particular, carbocations stabilized by neutral heteroatoms and those destabilized by their protonated forms, i. e., onium groups.

Report

(3 results)
  • 1997 Annual Research Report   Final Research Report Summary
  • 1996 Annual Research Report
  • Research Products

    (14 results)

All Other

All Publications (14 results)

  • [Publications] Saito, Ohwada, Shudo: "Super acid-catalyzed Reaction of Substituted Benzold ehydis with benzene" J.Organic chemistry. 118. 6220-6224 (1996)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Yokoyama, Ohwada, Saito, Shudo: "Nitration of Quinoline 1-Oxides meckanism of Regio-selectivity" Chem.Pharm.Bull.45. 279-283 (1997)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Suzuki, Ohwada, Shudo: "Super acid-catalyzed Electiocy clizution of 1-Phenyl-2-propene-1-ones to 1-In dones." J.Am.Chem.Soc.119. 6774-6780 (1997)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Ohwada, Suzuki, Shudo: "Super acid -catalyzed Electiocy clizution of Dipkenyl methyl cations to Flciorenes" J.Am.Chem.Soc. 120(in press). (1998)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Shudo, Ohwada: "Stable Cavbo cution chemistry" John Wiley & Sons, 525-548 (1997)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Saito, S. ; Ohwada, T. ; Shudo, K.: ""Superacid-Catalyzed Reaction of Substituted Benzaldehydes with Benzene"" Journal of Organic Chemistry. 61. 8089-8093 (1996)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Ohwada, T, ; Yamazaki, T. ; Suzuki, T. ; Satio, S. ; Shudo, K.: ""Structures and Reactivities of Ethylene Dication Electrophiles"" Journal of the American Chemical Society. 118. 6220-6224 (1996)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Yokoyama, A. ; Ohwada, T. ; Saito, S. ; Shudo, K.: ""Nitration of Quinoline 1-Oxide : Mechanism of Regioselectivity"" Chemical and Pharmaceutical Bulletin.45. 279-283 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Suzuki, T. ; Ohwada, T. ; Shudo, K.: ""Superacid-catalyzed Electrocyclization of 1-Phenyl-2-propene-1-ones to 1-Indanones. Kinetic and Theoretical Studies of Electrocyclization of Oxonium Carbenium Dications"" Journal of the American Chemical Society. 119. 6774-6780 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Ohwada, T. ; Suzuki, T. ; Shudo, K.: ""Superacid-catalyzed Electrocyclization of Diphenylmethyl Cations to Fluorenes. Kinetic and Theoretical Revisit Supporting the Involvement of Ethylene Dications"" Journal of the American Chemical Society. (in press). (1998)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Shudo, K. ; Ohwada, T.: Stable Carbocation Chemistry. John Wiley & Sons, Inc.Prakash, K.S. ; Schleyer, P.v.R.(ed), 525-548 (1997)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1997 Final Research Report Summary
  • [Publications] Ohwada, Suzuki, Shudo: "Super acid-catalyzed Electrocyclization of the Diphemylmethyl cations to Fluorenes." J.Am.Chem.Soc.120 (in press). (1998)

    • Related Report
      1997 Annual Research Report
  • [Publications] Suzuki, ohwada, Shudo: "Superacid-catalyzed Electrocyclization of 1-phenyl-2-propeur-i-ones to 1-Ind anones" J.Am.Chem.Soc.119. 6774-6780 (1997)

    • Related Report
      1997 Annual Research Report
  • [Publications] Ohwada,T,Yamazaki,T Suzuki,T,Saito,S,Shudo,K: "Structures and Reactivities of Ethylene Dication Electropciles" J.Am.Chem.Soc.118. 6220-6224 (1996)

    • Related Report
      1996 Annual Research Report

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Published: 1996-04-01   Modified: 2016-04-21  

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