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A new method of synthesizing macrocyclic compounds

Communication 9. Quantitative method of studying the intramolecular alkylation of 2-(ω-haloalkyl)-5-(carbethoxyacetyl)thiophenes in the presence of calcium carbonate

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

Conclusions

  1. 1.

    A quantitative method was developed for the investigation of the intramolecular alkylation of 2-(9-iodononyl)-5-(carbethoxyacetyl)thiophene in the presence of K2CO3, combining potentiometric microtitration of I− and a quantitative determination of 2-carbethoxy-[11]-α-cyclothionene by the method of gas-liquid chromatography.

  2. 2.

    The rate of intramolecular alkylation of 2-(9-iodononyl)-5-(carbethoxyacetyl) thiophene in methyl ethyl ketone in the presence of solid K2CO3 increases with increasing rate of mixing, reaching a maximum at 1000–1200 rpm.

  3. 3.

    In the presence of solid K2CO3 in methyl ethyl ketone, 2-(9-iodononyl)-5-(carbethoxyacetyl) thiophene is alkylated only intramolecularly; moreover, the polycondensation products are absent.

  4. 4.

    The data obtained support the assumption that intramolecular alkylation occurs on the surface of solid K2CO3.

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Literature cited

  1. S. Z. Taits and Ya. L. Gol'dfarb, Izv. AN SSSR, Otd. Khim. N.,1960, 1698.

  2. Ja. L. Goldfarb, S. Z. Taits, and L. J. Belenkii, Tetrahedron,19, 1851 (1963).

    Google Scholar 

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

  4. S. Z. Taits and Ya. L. Gol'dfarb, USSR Patent No. 13, 221; Byull. Izobr. No. 19 (1960).

  5. H. Hunsdiecker, Ber.,75, 1190 (1942);76, 142 (1943).

    Google Scholar 

  6. H. Hunsdiecker and H. Erlbach, Ber.,80, 129 (1947).

    Google Scholar 

  7. L. Claisen and E. Haase, Ber.,33, 3728 (1900).

    Google Scholar 

  8. V. L. Hansley, U.S. Patent No. 2, 228, 268; Chem. Abstrs.,35, 2534 (1941); V. Prelog, L. Frenkel, M. Kobelt, and P. Barman, Helv. Chim. Acta,30, 1741 (1947); V. Prelog, J. Chem. Soc.,1950, 420; M. Stoll and J. Mulstkamp, Helv. Chim. Acta,30, 1815 (1947).

    Google Scholar 

  9. S. Z. Taits, L. I. Belen'kii, and Ya. L. Gol'dfarb, Izv. Akad. Nauk SSSR, Ser. Khim.,1963, 1460.

  10. W. Schöniger, Microchim. Acta,1956, 869.

  11. V. A. Klimova and M. D. Vitalina, Zh. Analiticheskoi Khim.,15, 339 (1960).

    Google Scholar 

  12. Ya. L. Gol'dfarb, S. Z. Taits, and L. I. Belen'kii, Zh. Obshch. Khim.,29, 3564 (1959).

    Google Scholar 

  13. V. I. Yakerson, S. Z. Taits, and F. D. Alashev, Izv. Akad. Nauk SSSR, Ser. Khim.,1966, 1931.

  14. A. Simon and U. Uhlig, Ber.,85, 990 (1952).

    Google Scholar 

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Authors and Affiliations

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

    S. Z. Taits, É. A. Krasnyanskaya & Ya. L. Gol'dfarb

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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Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 4, pp. 754–762, April, 1968.

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Taits, S.Z., Krasnyanskaya, É.A. & Gol'dfarb, Y.L. A new method of synthesizing macrocyclic compounds. Russ Chem Bull 17, 728–734 (1968). https://doi.org/10.1007/BF00905741

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  • DOI: https://doi.org/10.1007/BF00905741

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