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Synthesis of macrocyclic compounds Communication 17. Effect of nature of cation of alkali metal carbonate on intramolecular alkylation of 2-(Ω-halcalkyl)-5-(carbethoxyacetyl)thiophenes

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Conclusions

  1. 1.

    In the intramolecular alkylation of 2-(9-iodononyl)-5-(carbethoxyacetyl)thiophene (la) in the presence of various alkali metal carbonates the cyclization rate increases with increase in the radius of the alkali metal cation and the surface area of the carbonate.

  2. 2.

    A parallel reaction of intermolecular condensation is observed when the concentration of the iodide (Ia) is increased above a value that is characteristic for each carbonate.

  3. 3.

    Taking into account the value of the surface area of the carbonate and the size of the alkali metal cation, a method was proposed for calculating the value of the initial concentration of the iodide (Ia), needed for selective intramolecular alkylation; the data obtained are in good agreement with the values of the initial concentrations found experimentally.

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Literature cited

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    S. Z. Taits and Ya. L. Gol'dfarb, Izv. Akad. Nauk SSSR, Otd. Khim. Nauk, 1698 (1960); Author's Certificate No. 132221; Byull. Izobr., No. 19, 21 (1960).

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    Ya. L. Gol'dfarb, S. Z. Taits, and V. N. Bulgakova, Izv. Akad. Nauk SSSR, Ser. Khim., 1299 (1963).

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Additional information

Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 8, pp. 1807–1814, August, 1973.

The authors wish to thank V. I. Lebedev for analyzing the alkali metal carbonates by the flame photometry method.

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Taits, S.Z., Krasnyanskaya, é.A., Klyachko-Gurvich, A.L. et al. Synthesis of macrocyclic compounds Communication 17. Effect of nature of cation of alkali metal carbonate on intramolecular alkylation of 2-(Ω-halcalkyl)-5-(carbethoxyacetyl)thiophenes. Russ Chem Bull 22, 1751–1756 (1973). https://doi.org/10.1007/BF00932107

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Keywords

  • Iodide
  • Alkylation
  • Rate Increase
  • Alkali Metal
  • Metal Cation