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Synthesis of ortho-substituted ethynylbenzenes

Conclusions

  1. 1.

    The condensation of o-substituted iodobenzenes, andα- andβ-iodonaphthalene, with ethyl 2-methyl-3-butyn-2-yl acetacetal, followed by hydrolysis and subsequent alkaline cleavage of the obtained alcohols, gave the corresponding ethynylarenes.

  2. 2.

    Aryl iodides, containing electron-acceptor groups in the o-position of the benzene ring, are more reactive in the acetylenic condensation than the unsubstituted iodobenzene.

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Literature cited

  1. 1.

    M. S. Shvartsberg, A. A. Moroz, and I. L. Kotlyarevskii, Izv. Akad. Nauk SSSR, Ser. Khim., 1306 (1971).

  2. 2.

    M. S. Shvartsberg and A. A. Moroz, Izv. Akad. Nauk SSSR, Ser. Khim., 1582 (1971).

  3. 3.

    J. Heilbron (editor), Dictionary of Organic Compounds pussian translation], IL (1949).

  4. 4.

    C. D. Cook and S. S. Danyluk, Tetrahedron,19, 177 (1963).

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Additional information

Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No.2, pp. 476–479, February, 1973.

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Moroz, A.A., Shvartstaerg, M.S. Synthesis of ortho-substituted ethynylbenzenes. Russ Chem Bull 22, 464–466 (1973). https://doi.org/10.1007/BF00851025

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Keywords

  • Alcohol
  • Hydrolysis
  • Ethyl
  • Benzene
  • Iodide