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The Organic Reactions and Synthesis based on the Utilization of Carbon Monoxide

Research Project

Project/Area Number 02650615
Research Category

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

Allocation TypeSingle-year Grants
Research Field 有機工業化学
Research InstitutionKASAI UNIVERSITY

Principal Investigator

HAMANAKA Sawako  KANSAI Univ.. Engineering, Professor, 工学部, 教授 (90067611)

Co-Investigator(Kenkyū-buntansha) NISHIYAMA Yutaka  KANSAI Univ., Engineering, Lecturer, 工学部, 専任講師 (30180665)
Project Period (FY) 1990 – 1992
Project Status Completed (Fiscal Year 1992)
Budget Amount *help
¥2,000,000 (Direct Cost: ¥2,000,000)
Fiscal Year 1992: ¥300,000 (Direct Cost: ¥300,000)
Fiscal Year 1991: ¥400,000 (Direct Cost: ¥400,000)
Fiscal Year 1990: ¥1,300,000 (Direct Cost: ¥1,300,000)
KeywordsCarbon Monoxide / Hydrogen Selenide / Dibromination / Diorganylselenides / Selenocarboxylates / Aluminum Halide / Phenylalkylcarbocations / Adamantanecarboxaldehyde / フェニル置換α,βージケトン / アダマンタン / アダマンタンカルボキシルアルデヒド / ジアルキルセレニド / ジアルキルジセレニド / セレノカルボキシレ-ト / アダマンタンカルボキシアルデヒド / ベンゼニウムイオン / セレニウム触媒 / カルボニル基の還元 / ジフェニルアルカン / フェニルアルキルカチオン / 塩化アルミニウム触媒 / インダノンの合成
Research Abstract

1. Synthesis utilization reducing ability of carbon monoxide, - Using CO/H_2O/Se reaction system-
(1) In the reductive dibromination of vic-dibromoalkanes with CO and H_2O in the presence of a catalytic amount of Se, vic-dibromoalkanes were converted to the corresponding alkanes in good yields and stereospecific.
(2) The selective generation of tertiary amine salts of hydrogen selenide and diselenide has been achived by controlling the reaction conditions. Diorganylselenides and diorganyldiselenides were synthesized in good yields with perfect selectivity.
(3) Phenyl substituted alpha- and beta-diketones were reduced to corresponding aromatic ketones in moderate to good yields.
2. Utilization of carbon monoxide as a useful agentas for introducing carbonyl functions into organic molecules.
(1) Treatment of 1, 1- or 1, 2-diphenylalkanes in benzene with AlCl_3-HCl formed the red-oil involving a phenylalkylcarbocations. When carbon monoxide was introduced to the red-oil, the phenylalkylcarbocations reacted with carbon monoxide to give 2-disubstituted-1-indanones via cyclization of the resulting acylcation.
(2) 1-adamantanecarboxaldehyde was synthesized by the AlI_3-catalyzed reaction of adamantane with CO in CH_2Cl_2 at < 25゚C

Report

(4 results)
  • 1992 Annual Research Report   Final Research Report Summary
  • 1991 Annual Research Report
  • 1990 Annual Research Report
  • Research Products

    (15 results)

All Other

All Publications (15 results)

  • [Publications] Yutaka NISHIYAMA: "Selenium-Catalyzed Debromination of vic-Dibromoalkanes and α-Bromo Ketones with Carbon Monoxide and Water" Heteroatom Chemistry. 1. 467-473 (1990)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] 岡田 隆志: "塩化アルミニウムによるジフェニルアルカンと一酸化炭素との反応" Chemistry Express. 5. 293-296 (1990)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] Yutaka NISHIYAMA: "Synthesis Utilizing Reducing Ability of Carbon Monoxide:A New Method for Selective Synthesis of Diorganyl Selenides and Diselelenides Using a Selenium-Carbon Monoxide-Water Reaction System" Journal of Organic Chemistry. 56. 3776-3780 (1991)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] Yutaka NISHIYAMA: "Selebium-Assisted Reduction of α-and β-Diketones with Carbon Monoxide and Water" Tetrahedoron Letters. 33. 6347-6350 (1992)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] 林 敬人: "1-アダマンタンカルボキシアルデヒドの合成" 石油学会誌.

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] Yutaka Nishiyama: "Selenium-Catalyzed Debromination of vic-Dibromoalkanes and alpha-Bromo Ketones with Carbon Monoxide and Water" Heteroatom Chemistry. 1-6. 467-473 (1990)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] Takashi Okada: "Reactions of Diphenylalkanes with Carbon Monoxide in the presence of AlCl_3-HCl" Chemistry Express. 5-5. 293-296 (1990)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] Yutaka Nishyama: "Synthesis Utilizing Reducing Ability of Carbon Monoxide : A New Method for Selective Synthesis of Diorganyl Selenides and Diselenides Using a Selenium-Carbon M anoxide-Water Reaction System" Journal of Organic Chemistry. 56-12. 3776-3780 (1991)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] Yutaka Nishiyama: "Selenium-Assisted Reduction of alpha- and beta-Diketones with Carbon Monoxide and Water" Tetrahedoron Letters. 33-42. 6347-6350 (1992)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] Yoshito Hayashi: "Synthesis of 1-Adamantanecarboxaldehyde" J.Jpn. Petrd. Inst.

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1992 Final Research Report Summary
  • [Publications] 西山 豊 浜中 佐和子 他3名: "Selemiun-Assisted Reduction of α‐and β‐Diketones with Carbon Monoxide and Water" Tetra hedron Lettcrs. 33. 6347-6350 (1992)

    • Related Report
      1992 Annual Research Report
  • [Publications] 西山 豊,浜中 佐和子 他6名: "Synthesis Utilizing Reducing Ability of Carbon Monoxide:A New Method for Selective Synthesis of Diorganyl Selenides and Diselenides Using a SeleniumーCarbon MonoxideーWater Reaction System" J.Org.Chem.56. 3776 (1991)

    • Related Report
      1991 Annual Research Report
  • [Publications] 浜中 佐和子 他2名: "ハロゲン化アルミニウム触媒によるアルキルベンゼンと二酸化炭素との反応" 技苑(関西大学工業技術研究所発行). 68. 16-20 (1991)

    • Related Report
      1991 Annual Research Report
  • [Publications] Yutaka,Nishiyama: "SeleniumーCatalyzed Debromination of vicーDibromoalkanes and αーBronio Ketones with Carbon Monoxide and Water" Heteroatom Chemistry. 1. 467-473 (1990)

    • Related Report
      1990 Annual Research Report
  • [Publications] 岡田 隆志: "塩化アルミニウムによるジフェニルアルカンと一酸化炭素との反応" Chemistry Express.5. 293-296 (1990)

    • Related Report
      1990 Annual Research Report

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Published: 1990-04-01   Modified: 2016-04-21  

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