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Properties and Reaction of π-Conjugated Carbonyl Compounds

Research Project

Project/Area Number 12640512
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeSingle-year Grants
Section一般
Research Field Organic chemistry
Research InstitutionSaitama University

Principal Investigator

HASEGAWA Toshio  Saitama Unniversity, Faculty of Science, Assistant Professor, 理学部, 助教授 (00237976)

Co-Investigator(Kenkyū-buntansha) MACHIGUCHI Takahisa  Saitama Unniversity, Faculty of Science, Professor, 理学部, 教授 (00008864)
Project Period (FY) 2000 – 2002
Project Status Completed (Fiscal Year 2002)
Budget Amount *help
¥1,900,000 (Direct Cost: ¥1,900,000)
Fiscal Year 2002: ¥700,000 (Direct Cost: ¥700,000)
Fiscal Year 2001: ¥1,200,000 (Direct Cost: ¥1,200,000)
Keywordsmonothiotropolone / equilibrium / azulene / troponolid / activated methylene compound / カルボニル / π電子 / NMR / IR / 分子軌道法 / 共役 / トロポン / ベンザイン / Diels-Alder
Research Abstract

We have found the following results,
1. Novel solid-state propertie :
Tropolone exsits as an last equilibrium mixture of a ketone form and an enol form. This equilibrium of tropolone is extremely fast in solution, but is frozened on the NMR time scale in the solid state. Monthiotropolone is the sulfur analogue of tropolone. We have found that this compound exists as extremely fast equilibrium mixture both in solution and in the solid state. This novel behavior in the solid-state is found to be due to packing arrangement of monothiotropolone.
2. Azulene synthesis in the reaction of an activated trponoid compound with an activated methylene compound :
Reaction of activated troponoid compounds with activated methylene compounds gave azulenes in good yields. These reactions are useful methods to obtain azulene derivatives with polyfunctional groups in five-membered ring moiety. We investigated the reaction mechanism of 2-methoxytropone with malonouilrilc to give an azulene and found the detailed reaction path of many steps containing several equilibrium processes.

Report

(4 results)
  • 2002 Annual Research Report   Final Research Report Summary
  • 2001 Annual Research Report
  • 2000 Annual Research Report
  • Research Products

    (4 results)

All Other

All Publications (4 results)

  • [Publications] A.Ishiwata: "Norcaradiene Intermediates in Mass Spectral Fragmentations of Tropone and Tropothione"J. Chem. Soc., Perkin Trans. 2. 2202-2210 (2001)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] T.Machiguchi: "Innovation of Ketene Chemistry. Big Faults in Ketene History and the Solutions"CACS Form. 20. 29-38 (2001)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] A. Ishiwatai: "Norcaradiene Intermediates in Mass Spectral Fragmenrations of Tropone and Tropothione"J. Chem. Soc., Perkin Trans.. 2. 2202-2210 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2002 Final Research Report Summary
  • [Publications] T.Machiguchi: "Reinvesligation of Tropore-Beucyne Reation To Givp Dids-Alder Type Adduot"Proc.ISNA. 10. 251 (2001)

    • Related Report
      2001 Annual Research Report

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Published: 2001-04-01   Modified: 2016-04-21  

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