Catalysis of Elemental Selenium and Tellurium in the Formation of Thiophene Derivatives from Alkyne and Elemental Sulfur

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  • KAJITANI Masatsugu
    Department of Chemistry, Faculty of Science and Technology, Sophia University
  • OCHIAI Ryuji
    Department of Chemistry, Faculty of Science and Technology, Sophia University
  • KIKUCHI Rika
    Department of Chemistry, Faculty of Science and Technology, Sophia University
  • AKIYAMA Takeo
    Department of Chemistry, Faculty of Science and Technology, Sophia University
  • SUGIMORI Akira
    Department of Chemistry, Faculty of Science and Technology, Sophia University

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Other Title
  • アルキンと単体硫黄との反応によるチオフェン誘導体の生成におよぼす単体セレンおよび単体テルルの触媒作用
  • アルキントタンタイイオウ

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Abstract

Elemental selenium and tellurium were found to catalyze the formation of thiophene derivatives in the reaction of elemental sulfur with alkyne (dimethyl acetylenedicarboxylate [1 a] and diphenylacetylene [1 b]). In the reaction of 100 mmol of [1 a] with 40 mmol of S at 110°C for 24 h in the absence of selenium or tellurium, the yield of tetramethyl 2, 3, 4, 5-thiophenetetracarboxylate [2 a] was 5%, while the yields of [2 a] in the presence of 0.04, 0.48, and 4.0 mmol of Se were 22, 39, and 53%, respectively. Elemental tellurium acted as a catalyst. In the similar conditions the yield of [2 a] in the presence of 0.2 mmol of Te was 38%.<BR>In the thi ophene forming reaction catalyzed by (η-cyclopentadienyl) (1, 5-cyclooctadiene)cobalt(I) [4], elemental selenium promoted the reaction. The yield of [2 a] was 75%in the reaction of 100 mmol of [1 a] with 40 mmol of S at 110°C for 24 h in the presence of 0.2 mmol of [4] and 40 mmol of Se.<BR>In the reaction of [1 b] p (25 mmol) with S (10 mmol) at 140°C for 24 h, the presence of 10 mmol of Se increased the yield of 2, 3, 4, 5-tetraphenylthiophene from 2% (in the absence of Se) to 10%.

Journal

  • NIPPON KAGAKU KAISHI

    NIPPON KAGAKU KAISHI 1987 (7), 1464-1468, 1987-07-10

    The Chemical Society of Japan

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