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Organic Syntheses Involving Reactions of Acetylenes with Elemental Sulfur and Selenium

Research Project

Project/Area Number 03640437
Research Category

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

Allocation TypeSingle-year Grants
Research Field 有機化学一般
Research InstitutionSaitama University

Principal Investigator

HOSHINO Masamatsu  Saitama University, Department of Chemistry, Professor, 理学部, 教授 (20008808)

Co-Investigator(Kenkyū-buntansha) ISHII Akihiko  Saitama University, Department of Chemistry, Assistant, 理学部, 助手 (90193242)
NAKAYAMA Juzo  Saitama University, Department of Chemistry, Professor, 理学部, 教授 (90092022)
Project Period (FY) 1991 – 1993
Project Status Completed (Fiscal Year 1993)
Budget Amount *help
¥2,000,000 (Direct Cost: ¥2,000,000)
Fiscal Year 1993: ¥200,000 (Direct Cost: ¥200,000)
Fiscal Year 1992: ¥400,000 (Direct Cost: ¥400,000)
Fiscal Year 1991: ¥1,400,000 (Direct Cost: ¥1,400,000)
Keywords1, 2-Dithietes / 1, 2-Dithiocarbonyl compounds / 1, 2-Dieselnoxo compounds / Tetraarylthiophenes / Tetraarylselenophenes / Thieno[3, 2-b]thiophenes / Selenolo[3, 2-b]selenophenes / Bis(diethylamino)carbeniumdithiocarboxylate / 単体硫黄 / 単体セレン / チエノチオフェン / セレノロセレノフェン / 1,2-ジスルフィン / 1,2-ジセレノカルボニル化合物 / チエノチオフェンオリゴマー / 機能性化合物 / チオフェン / セレノフェン / 1、2ージチェット / 1、2ージチオキソ化合物 / αービススルフィン / アセチレン / テトラアリ-ルチオフェン / テトラアリ-ルセレノフェン / 1,2ージチエット / αージチオン / 電子材料
Research Abstract

1) A convenient symthesis of 1, 2-dithietes, which involves reaction of elemental sulfur with acetylenes carrying bulky substituents such as tert-butyl and 1-adamantyl, has been established.
2) It was found that ynamines such as bis(diethlamino)acetylene react with elemental sulfur to give the corresponding 1, 2-dithiocarbonyl compounds but not the 1, 2-dithietes. A similar reaction with elemental selenium was also found.
3) Convenient and practical syntheses of tetraarylthiophenes and tetraarylselenophenes, which involve reactions of diarylacetylenes with elemental sulfur and selenium, respectively, have been deveised. Application of the above method allowed the preparation of a star-burst type of thiophene oliogomers.
4) Acetylenediols such as 2, 5-dimethl-3-hexyne-2, 5-diol react with elemental sulfur to give substituted thieno[3, 2-b]shiophenes, thus providing a practical one-pot synthesis of thienothiophenes. The reaction is also applicable to the preparation of selenolo[3, 2-b]selenophenes.
5) 2-Chloro and 2-phenoxy substituted 1, 1-bis(diethylamino)ethylenes react with elemental sulfur to afford an inner salt, bis(diethylamino)carbeniumdithiocarboxylate in excellent yields.

Report

(4 results)
  • 1993 Annual Research Report   Final Research Report Summary
  • 1992 Annual Research Report
  • 1991 Annual Research Report
  • Research Products

    (22 results)

All Other

All Publications (22 results)

  • [Publications] J.Nakayama,K.Sawada,A.Ishii,M.Hoshino: "Tetra-2-thienyl-and Tetra-kis(5,2'-bithiophene-2-yl)thiophenes and Selenophenes" Heterocycles. 34. 1487-1490 (1992)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1993 Final Research Report Summary
  • [Publications] J.Nakayama,I.Akiyama: "Unexpected Formation of an Inner Salt,Bis(diethylamino)-carbeniumdithiocarboxylate,from 2-Chloro-or 2-Phenoxy Substituted 1,1-Bis(diethylamino)ethylenes and Elemental Sulfur" J.Chem.Soc.,Chem.Commun.1522 (1992)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1993 Final Research Report Summary
  • [Publications] J.Nakayama,K.S.Choi,I.Akiyama,M.Hoshino: "A Convenient Synthesis of 1,2-Dithietes and α-Dithiocarbonyl Compounds by Sulfuration of Acetylenic Compounds" Tetrahedron Lett.34. 115-118 (1993)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1993 Final Research Report Summary
  • [Publications] K.S.Choi,I.Akiyama,M.Hoshino,J.Nakayama: "A Convenient Synthesis of 1,2-Dithietes and 1,2-Dithioxo Compounds Stabilized by Buttressing and Resonance Effects,Respectively,by Sulfuration of Alkynes and Elemental Sulfur" Bull.Chem.Soc.Jpn.66. 623-629 (1993)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1993 Final Research Report Summary
  • [Publications] Sawada,Choi,Kuroda,Taniguchi,Ishii,Hoshino,Nakayama: "Preparation of Tetraarylthiophenes and Tetraarylselenophenes by Reactions of Diarylacetylenes with Elemental Sulfur and Selenium" Sulfur Letters. 15. 273-283 (1993)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1993 Final Research Report Summary
  • [Publications] K.S.Choi,K.Sawada,H.Dong,M.Hoshino,J.Nakayama: "A One-pot Synthesis of Substituted Thieno[3,2-b]thiophenes and Selenolo[3,2-b]selenophenes" Heterocycles. 38. 143-149 (1994)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1993 Final Research Report Summary
  • [Publications] J.Nakayama,A.Mizumura,I.Akiyama,T.Nishio,I.Iida: "Synthesis and Chracterization of Tetraarylethanediselenoamide" Chem.Lett.77-80 (1994)

    • Description
      「研究成果報告書概要(和文)」より
    • Related Report
      1993 Final Research Report Summary
  • [Publications] J.Nakayama, K.Sawada, A.Ishii, and M.Hoshino: "Tetra-2-thienyl-and Tetrakis(5, 2'-bithiophene-2-yl)-thiophenes and Selenophenes" Heterocycles. 34. 1487-1490 (1992)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1993 Final Research Report Summary
  • [Publications] J,Nakayama and I.Akiyama: "Unexpected Formation of an Inner Salt, Bis(diethylamino)carbeniumdithiocarvoxylate, from 2-Chloro- or 2-Phenoxy Substituted 1,1-Bis(diethylamino)ethylenes and Elemental Sulfur" J.Chem.Soc., Chem.Commun.1522 (1992)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1993 Final Research Report Summary
  • [Publications] J.Nakayama, K.S.Choi, I.Akiyama, and M.Hoshino: "A Convenient Sythesis of 1,2-Dithietes and alpha-Dithiocarbonyl Compounds by Sulfuration of Acetylenic Compounds" Tetrahedron Lett.34. 115-118 (1993)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1993 Final Research Report Summary
  • [Publications] K.S.Choi, I.Akiyama, M.Hoshino, and J.Nakayama: "A Convenient Synthesis of 1,2-Dithietes and 1,2-Dithioxo Compounds Stabilized byButtressing and Resonance Effescts, Respectively, by Sulfuration of Alkynes and Elemental Sulfur" Bull.Chem.Soc.Jpn.66. 623-629 (1993)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1993 Final Research Report Summary
  • [Publications] K.Sawada, K.S.Choi, M.Kuroda, T.Taniguchi, A.Ishii, M.Hoshino, and J.Nakayama: "Preparation of Tetraarylthiophenes and Tetraarylselenophenes by Reactions of Diaryiacetylenes with Elemental Sulfur and Selenium" Sulfur letters. 15. 273-283 (1993)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1993 Final Research Report Summary
  • [Publications] K.S.Choi, K.Sawada, H.Dong, M.Hoshino, and J.Nakayama: "A one-pot Synthesis of Substituted Thieno[3, 2-b]thiophenes and Selenolo[3, 2-b]selenophenes" Heterocycles. 143-149 (1994)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1993 Final Research Report Summary
  • [Publications] J.Nakayama, A.Mizumura, I.Akiyama, T.Nishio, and I.Iida: "Synthesis and Characterization of Tetraarylethanediselenoamide" Chem.Lett.77-80 (1994)

    • Description
      「研究成果報告書概要(欧文)」より
    • Related Report
      1993 Final Research Report Summary
  • [Publications] Choi,Sawada,Dong,Hoshino,Nakayama: "A One-pot Synthesis of Substituted Thieno[3,2-b]thiophenes and Selenolo[3,2-b]selenophenes" Heterocycles. 38. 143-149 (1994)

    • Related Report
      1993 Annual Research Report
  • [Publications] Nakayama,Mizumura,Akiyama,Nishio,Iida: "Synthesis and Characterization of Tetraethylethanediselenoamide" Chemistry Letters. 77-80 (1994)

    • Related Report
      1993 Annual Research Report
  • [Publications] Sawada,Choi,Kuroda,Taniguchi,Ishii,Hoshino,Nakayama: "Preparation of Tetraarylthiophenes and Tetraarylselenophenes by Reactions of Diarylacetylenes with Elemental Sulfur and Selenium" Sulfur Letters. 16. (1993)

    • Related Report
      1992 Annual Research Report
  • [Publications] J.Nakayama,K.Sawada,A.Ishii,and M.Hoshino: "Tetraー2ーthienylーand Tetakis(5,2'ーbithiopheneー2ーyl)thiophenes and Selenophenes" Heterocycles. 34. 1487-1490 (1992)

    • Related Report
      1992 Annual Research Report
  • [Publications] J.Nakayama,K.S.Choi,I.Akiyama,and M.Hoshino: "A Convenient Synthesis of 1,2ーDithietes and α-Dithiocarbonyl Compounds by Sulfuration of Acetylenic Compounds" Tetrahedron Letters. 34. 115-118 (1993)

    • Related Report
      1992 Annual Research Report
  • [Publications] K.S.Choi,I.Akiyama,M.Hoshino,and J.Nakayama: "A Convenient Synthesis of 1,2ーDithietes and 1,2ーDithioxo Compounds Stabilized by Buttressing and Resonance Effects,Respectively,by Sulfuration of Alkynes with Elemental Sulfur" Bull.Chem.Soc.Jpn.66. 623-629 (1993)

    • Related Report
      1992 Annual Research Report
  • [Publications] J.Nakayama,K.Sawada,A.Ishii,and M.Hoshino: "Tetraー2ーthienylー and Tetrakis(5,2'ーbithiopheneー2ーyl)ーthiophenes and Selenophenes" Heterocycles.

    • Related Report
      1991 Annual Research Report
  • [Publications] J.Nakayama,K.S.Choi,I.Akiyama,and M.Hoshino: "A Convenient Synthesis of 1,2ーDithietes and αーDithiocarbonyl Compounds" Journal of the American Chemical Society.

    • Related Report
      1991 Annual Research Report

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

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