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α-Ketothioketene dimers

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Conclusions

Whenβ,β-dichlorovinyl ketones are reacted with Na2S, NaSC(S)N(C2H5)2, KSC(S)OC2H5, and NaSCOCH3, two types of sulfur-containing heterocyclic compounds are formed: 1,3-dithietanes\(RCOCH = C\begin{array}{*{20}c} { / S} \\ { \setminus S} \\ \end{array} \begin{array}{*{20}c} \setminus \\ / \\ \end{array} C = CHCOR\) and 1,3-dithiols\(RCOCH = C\begin{array}{*{20}c} { / S---} \\ { \setminus S---} \\ \end{array} \begin{array}{*{20}c} {CH} \\ {||} \\ {CCOR} \\ \end{array} \), at which time the ratio of the products depends on the nature of the sulfur-containing nucleophilic reagent.

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Literature cited

  1. 1.

    G. A. Gavrilova, G. G. Levkovskaya, A. N. Mirskova, and Yu. L. Frolov, Summaries of the Eighth Siberian Conference on Spectroscopy [in Russian], Irkutsk Inst. Org. Khim., Sib. Otd., Akad. Nauk SSSR, Irkutsk (1972), p. 48.

  2. 2.

    G. A. Gavrilova, V. V. Keiko, G. G. Levkovskaya, A. N. Mirskova, and Yu. L. Frolov, Summaries of the Eighth Siberian Conference on Spectroscopy [in Russian], Irkutsk Inst. Org. Khim., Sib. Otd., Akad. Nauk SSSR, Irkutsk (1972), p. 48.

  3. 3.

    A. S. Atavin, G. G. Levkovskaya, and A. N. Mirskova, Zh. Org. Khim.,9, 318 (1973).

  4. 4.

    G. G. Levkovskaya, A. N. Mirskova, A. S. Atavin, and I. D. Kalikhman, Zh. Org. Khim.,10, 2293 (1974).

  5. 5.

    I. D. Kalikhman, G. G. Levkovskaya, L. I. Lavlinskaya, A. N. Mirskova, and A. S. Atavin, Izv. Akad. Nauk SSSR, Ser. Khim., 2235 (1973).

  6. 6.

    A. N. Nesmeyanov, O. A. Reutov, and A. S. Gudkova, Izv. Akad. Nauk SSSR, Otd. Khim. Nauk, 260 (1961).

  7. 7.

    E. Wayer and H. Krober, Z. Chem., 91 (1975).

  8. 8.

    M. S. Raasch, Chem. Commun., 577 (1966).

  9. 9.

    R. Raapch, Can. J. Chem.,46, 2251 (1968).

  10. 10.

    P. Yates, D. R. Moore, and T. R. Lynch, Can. J. Chem.,49, 1456 (1971).

  11. 11.

    P. Yates, T. R. Lynch, and L. S. Weiler, Can. J. Chem.,46, 365 (1968).

  12. 12.

    P. Yates, T. R. Lynch, and D. R. Moore, Can. J. Chem.,49, 1467 (1971).

  13. 13.

    T. R. Lynch, I. P. Mellor, S. C. Nyburg, and P. Yates, Tetrahedron Lett., 373 (1967).

  14. 14.

    K. P. Zeller, H. Meier, and E. Muller, Liebigs Ann. Chem.,766, 32 (1972).

  15. 15.

    W. Kirmse and L. Horner, Liebigs Ann. Chem.,614, 4 (1968).

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Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 9, pp. 2940–2048, September, 1976.

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Mirskova, A.N., Levkovskaya, G.G., Kalikhman, I.D. et al. α-Ketothioketene dimers. Russ Chem Bull 25, 1913–1919 (1976). https://doi.org/10.1007/BF00921720

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Keywords

  • Ketone
  • Heterocyclic Compound
  • Na2S
  • Nucleophilic Reagent