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Development of New Carbonylation Method by Carbon Monoxide and the Synthesis of Thiocarbonates

Research Project

Project/Area Number 15550096
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeSingle-year Grants
Section一般
Research Field Synthetic chemistry
Research InstitutionKansai University

Principal Investigator

NISHIYAMA Yutaka  Kansai University, Faculty of Engineering, Assistant Professor, 工学部, 助教授 (30180665)

Co-Investigator(Kenkyū-buntansha) 園田 昇  関西大学, 工学部, 教授 (20083983)
Project Period (FY) 2003 – 2005
Project Status Completed (Fiscal Year 2005)
Budget Amount *help
¥3,700,000 (Direct Cost: ¥3,700,000)
Fiscal Year 2005: ¥700,000 (Direct Cost: ¥700,000)
Fiscal Year 2004: ¥1,000,000 (Direct Cost: ¥1,000,000)
Fiscal Year 2003: ¥2,000,000 (Direct Cost: ¥2,000,000)
Keywordsselenium / carbon monoxide / carbonylation / organosulfur compound / 触媒 / チオカーボネート
Research Abstract

It was confirmed a unique catalytic ability of selenium on the reaction of dialkyl disulfides with carbon monoxide. The carbonylation of dialkyl disulfide with carbon monoxide was promoted by the selenium catalyst in the presence of DBU to give the corresponding dialkyl dithiocarbonates.
When dibutyl disulfide was allowed to react with carbon monoxide in the presence of selenium catalyst and DBU as a base at 80℃ for 6h, dibutyl dithiocarbonate, which was the carbonylated product of disulfide, was obtained in 92% yield. The yield of the dithiocarbonate was influenced by the tertiary amine used as a base. The carbonylation of dialkyl disulfides such as dipropyl, dihexyl, and didecyl disulfide also proceeded smoothly in the presence of selenium catalyst to give the corresponding dialkyl dithiocarbonates in good yields. For the reaction of disulfide bearing secondary alkyl chain, the yield of the product based on reacted disulfide was high ; however, the conversion of disulfide was lower that that of primary one. In the case of tertiary dialkyl disulfide, the formation of dialkyl dithiocarbonate was not confirmed and disulfide was recovered. On the contrast, in the case of diphenyl disulfide, the carbonylated product was not obtained at all and thiol was formed in moderate yield.

Report

(4 results)
  • 2005 Annual Research Report   Final Research Report Summary
  • 2004 Annual Research Report
  • 2003 Annual Research Report
  • Research Products

    (24 results)

All 2006 2005 2004 2003 Other

All Journal Article (23 results) Publications (1 results)

  • [Journal Article] A New Method for the Synthesis of 2-Aryl-1H-benzimidazoles : Selenium-Catalyzed Reductive N-Heterocyclization of Benzylidene (2-nitroaryl) amines with Carbon Monoxide2006

    • Author(s)
      Y.Nishiyama
    • Journal Title

      Synlett (1)

      Pages: 109-111

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] A New Method for the Synthesis of 2-Aryl-1H-benzimidazolese : Selenium-Catalyzed Reductive N-Heterocyclization of Benzylidene(2-nitroaryl)amines with Carbon Monoxide2006

    • Author(s)
      Y.Nishiyama, M.Fujimoto, N.Sonoda
    • Journal Title

      Synlett. (1)

      Pages: 109-111

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] A New Method for the Synthesis of 2-Aryl-1H-benzimidazoles : Selenium-Catalyzed Reductive N-Heterocyclization of Benzylidene (2-nitro-aryl) amines with Carbon Monoxide2006

    • Author(s)
      Y.Nishiyama
    • Journal Title

      Synlett (1)

      Pages: 109-111

    • Related Report
      2005 Annual Research Report
  • [Journal Article] Utilization of Phenyl Trialkylstannyl Selenides as a Promising Reagent for Introduction of the Phenylseleno Group2005

    • Author(s)
      Y.Nishiyama
    • Journal Title

      Mini-Reviews in Org. Chem. 2

      Pages: 147-155

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] A New Method for the Synthesis of Organotellurium Compounds by the Use of Reductive Cleavage of the Tellurim-Tellurium Bond with Lanthanum2005

    • Author(s)
      Y.Nishiyama
    • Journal Title

      Bull. Chem. Soc. Jpn. 78(2)

      Pages: 341-343

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] A Facile Method for the synthes'is of Thhiocarbamates : Palladium-Catalyzed Reaction of Disulfides, Amine, and Carbon Monoxide2005

    • Author(s)
      Y.Nishiyama
    • Journal Title

      J. Org. Chem. 70(7)

      Pages: 2551-2554

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] Reductive Debrominination of 1,2-Bis(bromomethyl) arenes Using Tetrakis (dimethylamino) ethylene (TDAE)2005

    • Author(s)
      Y.Nishiyama
    • Journal Title

      Tetrahedron Lett. 46

      Pages: 867-869

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] A New Method for Synthesis of S-Aryl-O-alkyl Thiolcarbonates : Selenium-Catalyzed Reaction of Alcohols with Carbon Monoxide and Diaryl Disulfides2005

    • Author(s)
      Y.Nishiyama
    • Journal Title

      Tetrahedron Lett. 46

      Pages: 7415-7417

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] Utilization of Phenyl Trialkylstannyl Selenide as a Promising Reagent for Introduction of the Phenylseleno Group2005

    • Author(s)
      Y.Nishiyama, N.Sonoda
    • Journal Title

      Mini-Reviews in Org.Chem. 2

      Pages: 147-155

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] A New Method for the Synthesis of Organotellurium Compounds by the Use of Reductive Cleavage of the Tellurium-Tellurium Bond with Lanthanum2005

    • Author(s)
      Y.Nishiyama, M.Okada, T.Nishino, N.Sonoda
    • Journal Title

      Bull.Chem.Soc.Jpn. 78(2)

      Pages: 341-343

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] A Facile Method for the Synthesis of Thiocarbamates : Palladium-Catalyzed Reaction of Disulfide, Amine, and Carbon Monoxide2005

    • Author(s)
      Y.Nishiyama, H.Kawamatsu, N.Sonoda
    • Journal Title

      J.Org.Chem. 70(7)

      Pages: 2551-2554

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] Reductive Debromination of 1,2-Bis(bromomethyl)arenes Using Tetrakis (dimethyl-amino)ethylene (TDAE)2005

    • Author(s)
      Y.Nishiyaina, H.Kawabata, A.Kobayashi, T.Nishino, N.Sonoda
    • Journal Title

      Tetrahedron Lett. 46

      Pages: 867-869

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] A New Method for the Synthesis of S-Aryl-O-alkyl Thiol-carbonates : Selenium-Catalyzed Reaction of Alcohols with Carbon Monoxide and Diaryl Disulfides2005

    • Author(s)
      Y.Nishiyaina, K.Maehira, J.Nakase, N.Sonoda
    • Journal Title

      Tetrahedron Lett. 46

      Pages: 7415-7417

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] A Facile Method for the Synthesis of Thiocarbomates : Palladium-Catalyzed Reaction of Disulfides, Amine, and Carbon Monoxide2005

    • Author(s)
      Y.Nishiyama
    • Journal Title

      The Journal of Organic Chemistry 70(7)

      Pages: 2551-2554

    • Related Report
      2005 Annual Research Report
  • [Journal Article] Reductive debrominination of 1,2-bis(bromomethyl)arenas using tetrakis (dimethylamino) ethylene (TDAE)2005

    • Author(s)
      Y.Nishiyama
    • Journal Title

      Tetrahedron Letters 46

      Pages: 867-869

    • Related Report
      2005 Annual Research Report
  • [Journal Article] A new method for synthesis of S-aryl-O-alkyl thiolcarbonates : selenium-catalyzed reaction of alcohols with carbon monoxide and diaryl disulfides2005

    • Author(s)
      Y.Nishiyama
    • Journal Title

      Tetrahedron Letters 46

      Pages: 7415-7417

    • Related Report
      2005 Annual Research Report
  • [Journal Article] Reductive debromination of 1,2-bis(bromomethyl)arenas using tetrakis(di-methylamino)ethylene (TDAE)2005

    • Author(s)
      Y.Nishiyama
    • Journal Title

      Tetrahedron Letters 46

      Pages: 867-869

    • Related Report
      2004 Annual Research Report
  • [Journal Article] A New Method for the Synthesis of Organotellurium Compounds by the Use of Reductive Cleavage of the Tellurium-Tellurium Bond with Lanthanum Metal2005

    • Author(s)
      Y.Nishiyama
    • Journal Title

      Bulltin Chemical Society of Japan 78(2)

      Pages: 341-343

    • NAID

      10014366962

    • Related Report
      2004 Annual Research Report
  • [Journal Article] A New Method for Synthesis of 1,3-Oxathiolan -2-ones by the Reaction of Epoxides with Sulfur and Carbon Monoxide2004

    • Author(s)
      Y.Nishiyama
    • Journal Title

      Tetrahedron Lett. 45

      Pages: 8539-8540

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] A New Method for the Synthesis of 1,3-Oxathiolane-2-ones by the Reaction of Epoxides with Sulfur and Carbon Monoxide2004

    • Author(s)
      Y.Nishiyaina, C.Katahira, N.Sonoda
    • Journal Title

      Tetrahedron Lett. 45

      Pages: 8539-8540

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] A new method for the synthesis of 1,3-oxathiolan-2-ones by the reaction of epoxides with sulfur and carbon monoxide2004

    • Author(s)
      Y.Nishiyama
    • Journal Title

      Tetrahedron Letters 45

      Pages: 8539-8540

    • Related Report
      2004 Annual Research Report
  • [Journal Article] Dehalogenation of ο-dihalogen substituted arenes and α,α-dihalogen substituted ο-xylene with lanthanum metal2003

    • Author(s)
      Y.Nishiyama
    • Journal Title

      Tetrahedron 59

      Pages: 6609-6614

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Journal Article] Dehalogenation of o-dihalogen substituted arenes and α,α-dihalogen substituted o-xylene with lanthanum metal2003

    • Author(s)
      Y.Nishiyaina, H.Kawabata, T.Nishino, K.Hashimoto, N.Sonoda
    • Journal Title

      Tetrahedron 59

      Pages: 6609-6614

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2005 Final Research Report Summary
  • [Publications] Y.Nishiyama, N.Sonoda: "A New Synthetic Method of 1,4-Dihydro-2H-3,1-benzoxazin-2-ones : Selenium-Catalyzed Reductive Carbonylation of Aromatic Nitro Compounds with Carbon Monoxide"Synlett. (印刷中). (2005)

    • Related Report
      2003 Annual Research Report

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Published: 2003-04-01   Modified: 2016-04-21  

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