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Non-conventional Aromatic Electrophilic Reactions Occurring via "ipso" Arenium Ion Intermediates

Research Project

Project/Area Number 60470024
Research Category

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

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

Principal Investigator

SUZUKI Hitomi  Professor, 理学部, 教授 (50025342)

Project Period (FY) 1985 – 1986
Project Status Completed (Fiscal Year 1986)
Budget Amount *help
¥7,700,000 (Direct Cost: ¥7,700,000)
Fiscal Year 1986: ¥500,000 (Direct Cost: ¥500,000)
Fiscal Year 1985: ¥7,200,000 (Direct Cost: ¥7,200,000)
KeywordsAromatics / Nitration / Electrophilic Reaction / 反応機構
Research Abstract

Non-conventional reactions of benzenoid compounds which occur as a consequence of "ipso" attack of electrophiles have been investigated, with a special emphasis on the elucidation of the anomalies observed during the side-chain nitration of polysubstituted arenes; nitrooxylation with <HNO_3> / <CH_2> <Cl_2> and nitration with <HNO_3> / <(CH_3CO)_2> O. Based on the evidence obtained from product variations with substituents, electrochemical nitrodecarboxylation of arylacetates, and ESR examination of the initial stage of the side-chain reactions, a proposal is made that the side-chain substitution of polysubstituted arenes occurs via heterolytic path with <HNO_3> / <CH_2> <Cl_2> and via a homolytic path with <HNO_3> / <(CH_3CO)_2> O. The first isolation of a proposed methylenecyclohexadiene intermediate for the side-chain substitution of arenes under heterolytic conditions is also included.

Report

(1 results)
  • 1986 Final Research Report Summary
  • Research Products

    (6 results)

All Other

All Publications (6 results)

  • [Publications] H.Suzuki;E.Kimura;T.Katayama;T.Ogawa: Chem.Lett.1987. (1987)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1986 Final Research Report Summary
  • [Publications] H.Suzuki;H.Koide;Y.Taki;E.Ohbayashi;T.Ogawa: Chem.Lett.1987. (1987)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1986 Final Research Report Summary
  • [Publications] H.Suziki;T.Ogawa: Seventh IUPAC Conference on Physical Organic Chemistry;Conference Abstracts. (1985)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1986 Final Research Report Summary
  • [Publications] H. Suzuki, E. Kimura, T. Katayama, and T. Ogawa: "9-Methyl-9-nitro-10-nitromethylene-9,10-dihydroanthracene. The First Isolation of a Proposed Intermediate for the Side-chain Nitration of Arenes under Heterolytic Conditions" Chem. Lett., 1987.

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1986 Final Research Report Summary
  • [Publications] H. Suzuki, H. Koide, Y. Taki, E. Ohbayashi, and T. Ogawa: "An Interpretation of the Puzzling Dichotomy of the Reaction Modes Observed during the Side-chain Nitration of Alkylaromatics with <HNO_3> / <CH_2> <Cl_2> and <HNO_3> / <(CH_3CO)_2> O" Chem. Lett., 1987, in press.

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1986 Final Research Report Summary
  • [Publications] H. Suzuki and T. Ogawa: "Non-conventional Nitration of Polyalkylbenzenes. Side-chain Nitrooxylation and Nitration" Seventh IUPAC Conference on Physical Organic Chemistry; Conference Abstracts. (1985)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1986 Final Research Report Summary

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Published: 1987-03-31   Modified: 2016-04-21  

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