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Synthesis of thiophene derivatives containing the tert-butyl group, and some of their properties

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Bulletin of the Academy of Sciences of the USSR, Division of chemical science Aims and scope

Summary

  1. 1.

    The conditions have been determined for the alkylation with tert-butyl chloride of 2-methylthiophene, 2-ethylthiophene, 2,5-dimethylthiophene, and 2,5-diethylthiophene, and as a result the following compounds have been synthesized: 2-tert-butyl-5-methylthiophene, 2-tert-butyl-5-ethylthlophene, 3,5-di-tert-butyl-2-methylthiophene, 3,5-di-tert-butyl-2-ethylthiophene, 3-tert-butyl-2,5-dirnethylthiophene, and 3-tert-butyl-2,5-diethylthiophene. The alkyl-substituted thiophenes were obtained in 85–95% yields.

  2. 2.

    The structures of these new tert-butyl-substituted thiophenes have been proved by acetylation in presence of stannic chloride.

  3. 3.

    It has been shown for the first time that, in the acetylation in presence of stannic chloride of trisubstituted thiophenes containing a tent-butyl group, the latter is eliminated when it occurs in the β-position.

  4. 4.

    5-tert-Butyl-2-methyl-3-thienyI methyl ketone and 5-tert-butyl-2-ethyl -3-thienyl methyl ketone have been synthesized.

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Authors and Affiliations

  1. N. D. Zelinsky Institute of Organic Chemistry of the USSR Academy of Sciences, USSR

    Ya. L. Goldfarb & I. S. Korsakova

Authors
  1. Ya. L. Goldfarb
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  2. I. S. Korsakova
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Goldfarb, Y.L., Korsakova, I.S. Synthesis of thiophene derivatives containing the tert-butyl group, and some of their properties. Russ Chem Bull 3, 481–485 (1954). https://doi.org/10.1007/BF01167830

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  • DOI: https://doi.org/10.1007/BF01167830

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