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Synthesis of macrocyclic compounds

Communication 19. Macrocyclic bis-(β-ketoesters) involving thiophene rings and selection of optimum conditions for their preparation

  • Organic and Biological Chemistry
  • Published:
Bulletin of the Academy of Sciences of the USSR, Division of chemical science Aims and scope

Conclusions

  1. 1.

    A study was made of the intramolecular aklylation of some 2-(ω-haloalkyl)-5-carbethoxyacetyl) thiophenes in the presence of K2CO3 in order to find the conditions for the selective formation of macrocyclic cyclodithiendiones.

  2. 2.

    The creation of conditions, where competition for the K2CO3 surface is possible, favors the formation of the macrocyclic bis-(β-ketoester), which has a double number of carbon atoms in the ring when compared with the number of carbon atoms in the starting compound.

  3. 3.

    Mathematical treatment by the statistical method of constructing a multiple regression reveals that a region exists where the yield of the macrocyclic bis-(β-ketoester) is optimum at 30–40%, which is in agreement with the experimental data.

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Authors and Affiliations

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

    S. Z. Taits, É. A. Krasnyanskaya, Ya. L. Gol'dfarb, N. F. Kononov, A. G. Pogorelov & R. F. Merzhanova

Authors
  1. S. Z. Taits
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  2. É. A. Krasnyanskaya
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  3. Ya. L. Gol'dfarb
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  4. N. F. Kononov
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  5. A. G. Pogorelov
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  6. R. F. Merzhanova
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Additional information

Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 11, pp. 2536–2544, November, 1975.

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Taits, S.Z., Krasnyanskaya, É.A., Gol'dfarb, Y.L. et al. Synthesis of macrocyclic compounds. Russ Chem Bull 24, 2422–2429 (1975). https://doi.org/10.1007/BF00921659

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  • DOI: https://doi.org/10.1007/BF00921659

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