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Investigation for comprehensive application of new selenating reagent, LiAlHSeH

Research Project

Project/Area Number 14540490
Research Category

Grant-in-Aid for Scientific Research (C)

Allocation TypeSingle-year Grants
Section一般
Research Field Organic chemistry
Research InstitutionGIFU UNIVERSITY

Principal Investigator

KOTETSU Mamoru  Gifu.Univ., Life Science Research Center, Associate Professor, 生命科学総合実験センター, 助教授 (50178208)

Project Period (FY) 2002 – 2003
Project Status Completed (Fiscal Year 2003)
Budget Amount *help
¥3,600,000 (Direct Cost: ¥3,600,000)
Fiscal Year 2003: ¥1,000,000 (Direct Cost: ¥1,000,000)
Fiscal Year 2002: ¥2,600,000 (Direct Cost: ¥2,600,000)
KeywordsSelenatin Reagent / Sulfur Transfer Reagent / Sulfur Compound / LiAlHSeH / Heteocyclic Compound / Heteroatom Chemistry / Selenium Compound / Carbamate / ジアシルスルフィド / ジチオカルバミン酸 / セレノチオカルバミン酸 / 有機合成 / ジセレノカルバミン酸 / セレノ尿素 / セレノアミド
Research Abstract

Recently, we have developed novel selenating reagent (LiAlHSeH) which is simple method, capable of preparing it only by stirring two kinds of agent in organic solvent. The LiAlHSeH formed in situ was ready for further reaction without concentration. The LiAlHSeH is capable of preparing a wide range of selenium-containing compounds in high yields and is novel selenium induction agent. (J.Am.Chem.Soc., 2001, 123, 8408)
We can prepare compounds having various basic skeletons by using the LIAlHSeH in high yields. We investigated preparation methods of selenium-containing compounds for two years of this study period. Furthermore, it was confirmed that similar reaction using also elemental sulfur progressed. It was clarified about expansibility of this reagent. In other words, after optimization of reaction conditions for compounds having basis skeleton such as selenourea, selenoamide, selenothiocarbamic acid, diacyl sulfide, dithiocarbamate, selenol ester, generality of reaction by extension of substrate and structural characteristic of the compounds were investigated, and then the results were published in academic papers. We investigated whether various reactions by using sulfur progressed. By optimum conditions of reaction temperature or activating agent were examined, we confirmed even sulfur could utilize as well as selenium.
In a Grant in Aid for Scientific Research in these two years, we prepared several compounds including group of unreported compounds, and were able to clarify their physicochemical characteristic. Those results were reported as papers more than 12 reports to academic journals including The Journal of American Chemical Society.

Report

(3 results)
  • 2003 Annual Research Report   Final Research Report Summary
  • 2002 Annual Research Report
  • Research Products

    (36 results)

All Other

All Publications (36 results)

  • [Publications] H.Ishihara, M.Koketsu, Y.Fukuta, F.Nada: "Reaction of lithium aluminum hydride with elemental selenium : Its application as a selenating reagent into organic molecules"Journal of American Chemical Society. 123. 8408-8409 (2001)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] M.Koketsu, Y.Fukuta, H.Ishihara: "Preparation of N,N-unsubstituted selenoureas and thioureas from cyanamides"Tetrahedron Letters. 42. 6333-6335 (2001)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] M.Koketsu, M.Ishida, N.Takakura, H.Ishihara: "Preparation and characterization of N-alkyl-Se-alkylselenocarbamates"Journal of Organic Chemistry. 67. 486-490 (2001)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] M.Koketsu, Y.Fukuta, H.Ishihara: "Reaction of N,N-dimethylselenocarbamoyl chloride with nucleophiles. Preparation of diselenocarbamates, selenothiocarbamates, and selenoureas"Journal of Organic Chemistry. 67. 1008-1011 (2002)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] M.Koketsu, F.Nada, H.Ishihara: "Facile preparation of 2-imino-1,3-selenazolidin-4-one derivatives by reaction of N,N'-disubstituted selenoureas with α-haloacyl halides"Synthesis. (2). 195-198 (2002)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] M.Koketsu, Y.Okayama, H.Aoki, H.Ishihara: "Facile synthesis of N,N-dialkylselenoamides from amides"Heteroatom Chemistry. 13. 195-198 (2002)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] M.Koketsu, F.Nada, S.Hiramatsu, H.Ishihara: "Reactions of acyl chlorides with LiAlHSeH. Preparation of diacyl selenides, diacyl diselenides, selenocarboxylates and cyclic selenoanhydrides"Journal of chemical Society, Perkin Transaction 1. (6). 737-740 (2002)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] M.Koketsu, N.Takakura, H.Ishihara: "Efficient synthesis of selenoureas from the corresponding carbodiimides"Synthetic Communications. 32. 3075-3079 (2002)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] M.Koketsu, F.Nada T.Mio, H.Ishihara: "Synthesis of 4-selenazolones. Hetero Diels-Alder reaction of selenazadienes with DMAD"Heterocycles. 60. 1211-1218 (2003)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] M.Koketsu, C.Kobayashi, H.Ishihara: "Synthesis of N-aryl S-alkylthiocarbamates"Heteroatom Chemistry. 14. 374-378 (2003)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] M.Koketsu, Y.Sekiya, H.Ishihara: "A convenient synthesis of diacyl sulfides using a novel sulfur transfer reagent"Heteroatom Chemistry. 14. 633-635 (2003)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] M.Koketsu, T.Otsuka, H.Ishihara: "Synthesis of dithiocarbamates and selenothiocarbamates"Phosphorus, Sulfur and Silicon. 179. 443-448 (2004)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] M.Koketsu, H.Asada, H.Ishihara: "Synthesis of selenol esters using acyl halides and a novel selenating reagent, LiAlHSeH"Phosphorus, Sulfur and Silicon. 179. 591-595 (2004)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] H.Ishihara, M.Koketsu, Y.Fukuta, F.Nada: "Reaction of lithium aluminum hydride with elemental selenium : Its application as a selenating reagent into organic molecules,"Journal of American Chemical Society. 123(34). 8408-8409 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] M.Kotetsu, Y.Fukuta, H.Ishihara: "Preparation of N,N-unsubstituted selenoureas and thioureas from cyanamides"Tetrahedron Letters. 42(36). 6333-6335 (2001)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] M.Koketsu, M.Ishida, N.Takakura, H.Ishihara: "Preparation and characterization of N-alkyl-Se-alkylselenocarbamates,"Journal of Organic Chemistry. 67(2). 486-490 (2002)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] M.Kotetsu, Y.Fukuta, H.Ishihara: "Reaction of N,N-dimenthylselenocarbamoyl chloride with nucleophiles. Preparation of diselenocarbamates, selenothiocarbamates, and selenoureas,"Journal of Organic Chemistry. 67(3). 1008-1011 (2002)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] M.Kotetsu, F.Nada, H.Ishihara: "Facile preparation of 2-imino-1,3-selenazolidin-4-one derivatives by reaction of N,N'-disubstituted selenoureas with α-haloacyl halides,"Synthesis. (2). 195-198 (2002)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] M.Koketsu, Y.Okayama, H.Aoki, H.Ishihara: "Facile synthesis of N,N-dialkylselenoamides from amides,"Heteroatom Chemistry. 13(3). 195-198 (2002)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] M.Koketsu, F.Nada, S.Hiramatsu, H.Ishihara: "Reactions of acyl chlorides with LiAlHSeH. Preparation of diacyl selenides, diacyl diselenides, selenocarboxylates and cyclic selenoanhydrides"Journal of Chemical Society, Perkin Transaction 1. (6). 737-740 (2002)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] M.Koketsu, N.Takakura, H.Ishihara: "Efficient synthesis of selenoureas from the corresponding carbodiimides,"Synthetic Communications,. 32(19). 3075-3079 (2002)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] M.Kotetsu, F.Nada, T.Mio, H.Ishihara: "Synthesis of 4-selenazolones. Hetero Diels-Alder reaction of slelnazadienes with DMAD,"Heterocycles. 60(5). 1211-1218 (2003)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] M.Kotetsu, C.Kobayashi, H.Ishihara: "Synthesis of N-aryl S-alkylthiocarbamates,"Heteroatom Chemistry. 14(4). 374-378 (2003)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] M.Kotestu, Y.Sekiya, H.Ishihara: "A convenient synthesis of diacyl sulfides using a novel sulfur transfer reagent"Heteroatom Chemistry. 14(7). 633-635 (2003)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] M.Kotestu, T.Otsuka, H.Ishihara: "Synthesis of dithiocarbamates and selenothiocarbamates,"Phosphorus, Sulfur and Silicon,. 179(3). 443-448 (2004)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] M.Kotetsu, H.Asada, H.Ishihara: "Synthesis of selenol esters using acyl halides and a novel selenating reagent, LiAlHSeH"Phosphorus, Sulfur and Silicon,. 179(3). 591-595 (2004)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      2003 Final Research Report Summary
  • [Publications] M.Koketsu, F.Nada, T.Mio, H.Ishihara: "Synthesis of 4-selenazolones. Hetero Diels-Alder reaction of selenazadienes with DMAD"Heterocycles. 60. 1211-1218 (2003)

    • Related Report
      2003 Annual Research Report
  • [Publications] M.Koketsu, C.Kobayashi, H.Ishihara: "Synthesis of N-aryl S-alkylthiocarbamates"Heteroatom Chemistry. 14. 374-378 (2003)

    • Related Report
      2003 Annual Research Report
  • [Publications] M.Koketsu, Y.Sekiya, H.Ishihara: "A convenient synthesis of diacyl sulfides using a novel sulfur transfer reagent"Heteroatom Chemistry. 14. 633-635 (2003)

    • Related Report
      2003 Annual Research Report
  • [Publications] M.Koketsu, T.Otsuka, H.Ishihara: "Synthesis of dithiocarbamates and selenothiocarbamates"Phosphorus, Sulfur and Silicon. (In press).

    • Related Report
      2003 Annual Research Report
  • [Publications] M.Koketsu, H.Asada, H.Ishihara: "Synthesis of selenol esters using acyl halides and a novel selenating reagent, LiAlHSeH"Phosphorus, Sulfur and Silicon. (In press).

    • Related Report
      2003 Annual Research Report
  • [Publications] M.Koketsu, M.Ishida, N.Takakura, H.Ishihara: "Preparation and characterization of N-alkyl-Se-alkylcarbamates"Journal of Organic Chemistry. 67. 486-490 (2002)

    • Related Report
      2002 Annual Research Report
  • [Publications] M.Koketsu, Y.Fukuta, H.Ishihara: "Reaction of N, N-dimethylselenocarbamoyl chloride with nucleophiles. Preparation of diselenocarbamates, selenothiocarbamates and selenoureas"Journal of Organic Chemistry. 67. 1008-1011 (2002)

    • Related Report
      2002 Annual Research Report
  • [Publications] M.Koketsu, Y.Okayama, H.Aoki, H.Ishihara: "Facile synthesis of N, N-dialkylselenoamide from amide"Heteroatom Chemistry. 13. 195-198 (2002)

    • Related Report
      2002 Annual Research Report
  • [Publications] M.Koketsu, F.Nada, S.Hiramatsu, H.Ishihara: "Reactions of acyl chlorides with LiAlHSeH. Preparation of diacyl selenides diacyl diselenides, selenocarboxylates and cyclic selenoanhydrides"Journal of Chemical Society, Perkin Transaction 1. 737-740 (2002)

    • Related Report
      2002 Annual Research Report
  • [Publications] M.Koketsu, N.Takakura, H.Ishihara: "Efficient synthesis of selenoureas from the corresponding carbodiimides"Synthetic Communications. 32. 3075-3079 (2002)

    • Related Report
      2002 Annual Research Report

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Published: 2002-04-01   Modified: 2016-04-21  

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