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1992 Fiscal Year Final Research Report Summary

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
KeywordsWilkinson catalyst / Homogeneous hydrogenation / 4-Thiochromone / 4-Thiochromanone / Selective hydrogenation
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.

  • Research Products

    (5 results)

All Other

All Publications (5 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
  • [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
  • [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
  • [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
  • [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

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Published: 1994-03-24  

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