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1993 Fiscal Year Final Research Report Summary

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
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
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.

  • Research Products

    (14 results)

All Other

All Publications (14 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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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
  • [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

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Published: 1995-03-27  

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