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Selective Hydrogenation of Cyclic alpha,beta-unsaturated ketones containing sulfur atom with the Wilkinson type Catalyst.

Research Project

Project/Area Number 03640434
Research Category

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

Allocation TypeSingle-year Grants
Research Field 有機化学一般
Research InstitutionMiyagi University of Education

Principal Investigator

HANAYA Kaoru  Miygi University of Education, Faculty of Education, Professor, 教育学部, 教授 (40006937)

Project Period (FY) 1991 – 1992
Project Status Completed (Fiscal Year 1992)
Budget Amount *help
¥1,800,000 (Direct Cost: ¥1,800,000)
Fiscal Year 1992: ¥300,000 (Direct Cost: ¥300,000)
Fiscal Year 1991: ¥1,500,000 (Direct Cost: ¥1,500,000)
KeywordsWilkinson catalyst / Homogeneous hydrogenation / 4-Thiochromone / 4-Thiochromanone / Selective hydrogenation / 4ーチオクロモン誘導体
Research Abstract

The hydrogenation of 4-thiochromones [1], 3-benzyliden-4-thiochromanones [2] and these 1,1-dioxides [3], [4] by the Wilkinson rhodium catalyst was examined and was obtained the results as follows.
1.Wilkinson catalyst is inactive for [1] and starting material was recovered nearly quantitatively except 2-methy1-4-chromone which hydrogenated to corresponding thiochromanone in Ca. 30% yield.
2.The hydrogenation of 2,3-dimethy1-4-thiochromone gave the 1:1 mixture of cis- and trans-2,3-dimethy1-4-chromanone.
3.The hydrogenation [3] and [4] gave the corresponding 4-thio-chromanone 1,1-dioxide in a high yield, respectively.
4.The hydrogenation [2] gave the corresponding 3-benzy1-4-thio-chromanone (30-40%) along with the isomerized product (3-benzy1-4-thiochromone, 10-15%).
From these results, the behavioral difference of [1] and [2], [1] and [3] in the hydrogenation with Wilkinson catalyst and a mechanism of the hydrogenation with Wilkinson catalyst was discussed.

Report

(3 results)
  • 1992 Annual Research Report   Final Research Report Summary
  • 1991 Annual Research Report
  • Research Products

    (10 results)

All Other

All Publications (10 results)

  • [Publications] 花屋 馨,熊谷 麻美,佐々木 克敬,石山 純一: "4-チオクロモン誘導体の接触水素化" 第24回有機合成化学協会関東支部シンポジウム講演要旨集.

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] K.HANAYA,A.KUMAGAI,K.SASAKI,and J.ISHIYAMA: "Homogeneous Hydrogenation of 4-Thiochromones by the Wilkinson Rhodium Catalyst." Chem.& Ind.

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] 花屋 馨,赤平 祐子,佐々木 克敬,石山 純一: "4-クロモン誘導体の8族金属触媒による接触水素化" 日本化学会誌.

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] K. Hanaya, A. Kumagai, K. Sasaki, and J. Ishiyama: "Chemistry and Industry"

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] K. Hanaya, Y. Akahira, K. Sasaki, and J. Ishiyama: "J. Chem. Soc. Japn."

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] 花屋 馨・熊谷 麻美・佐々木 克敬・石山 純一: "4-チオクロモン誘導体の接触水素化" 第24回 有機合成化学協会関東支部シンポジウム,講演要旨集. 45

    • Related Report
      1992 Annual Research Report
  • [Publications] K.Hanaya,A.Kumagai,K.Sasaki,and J.Ishiyama: "Homogeneous Hydrogenation of 4-Thiochromones by the Wilkinson Rhodium Catalyst." Chem.& Ind.,.

    • Related Report
      1992 Annual Research Report
  • [Publications] 花屋 馨・赤平 祐子・佐々木 克敬・石山 純一: "4-クロモン誘導体の8族金属触媒による接触水素化" 日本化学会誌.

    • Related Report
      1992 Annual Research Report
  • [Publications] Kaoru HANAYA: "Homogeneous Hydrogenation of 4ーThiochromones with Wilkinson Rhodium catalyst" Chemistry&Industry. (1992)

    • Related Report
      1991 Annual Research Report
  • [Publications] 花屋 馨,熊谷 麻美: "4ーチオクロモンおよび4ーチオクロマノン誘導体のWilkinson型触媒による均一系水素化" 日本化学会誌. (1993)

    • Related Report
      1991 Annual Research Report

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Published: 1991-04-01   Modified: 2016-04-21  

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