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1-Chloro-2,6-dinitro-4-perfluoroalkylthiobenzenes in the Synthesis of Heterocycles

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

1-Chloro-2,6-dinitro-4-perfluoroalkylthiobenzenes was obtained in first time by perfluoroalkylation of bis(4-chloro-3,5-dinitrophenyl)disulfide in the presence of xenon bisperfluoroalkylcarboxylates. At the interaction of these compounds with potassium ethylxanthogenate only substitution of chlorine atom occurred. The reaction with sodium N,N-dimethyldithiocarbamate leads to the nucleophilic substitution of nitro group with formation of 1,3-benzodithiol-2-one, but on action of ethyl thioglycolate the intramolecular condensation occurs with formation of benzothiazoles N-oxides.

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REFERENCES

  1. R. E. Banks (editor), Organofluorine Chemicals and their Industrial Applications, Horwood Ltd, Chichester (1979), p. 125.

    Google Scholar 

  2. T. Fujita, J, Iwasa, and C. Hansch, J. Am. Chem. Soc., 86, 5175 (1964).

    Google Scholar 

  3. L. M. Yagupol′skii, Aromatic and Heterocyclic Compounds with Fluorine-Containing Substituents [in Russian], Naukova Dumka, Kiev (1988), p. 275.

    Google Scholar 

  4. A. M. Sipyagin, V. S. Enshov, C. P. Bateman, B. D. Mullen, and J. S. Thrasher, Abstracts of the Twelfth European Symposium on Fluorine Chemistry, Berlin, Germany (1998), PII-96.

  5. V. O. Lukashevich, Dokl. Akad. Nauk SSSR, 103, 627 (1955).

    Google Scholar 

  6. V. S. Enshov, S. A. Kashtanov, I. V. Efremov, I. A. Pomytkin, A. M. Sipyagin, and N. N. Aleinikov, Khim. Geterotsikl. Soedin., 1703 (1995).

  7. M. Yoshida, T. Yoshida, M. Kobayashi, and N. Kamigata, J. Chem. Soc. Perkin Trans. 1, 909 (1989).

  8. K. Rasheed and J. D. Warkentin, J. Org. Chem., 44, 267 (1979).

    Google Scholar 

  9. J. J. D'Amico, C. C. Tung, W. E. Dahl, D. J. Dahm, J. Org. Chem., 42, 2896 (1977).

    Google Scholar 

  10. A. M. Sipyagin and I. V. Efremov, Khim. Geterotsikl. Soedin., 1088 (1996).

  11. A. M. Sipyagin, S. V. Pal'tsun, A. V. Piyuk, N. N. Sveshnikov, V. I. Kozlovskii, and Z. G. Aliev, Zh. Org. Khim., 29, 1872 (1993).

    Google Scholar 

  12. K. Wagner, H. Heitzer, and L. Oehlmann, Chem. Ber., 106, 640 (1973).

    Google Scholar 

  13. N. S. Vul'fson, V. G. Zaikin, and A. I. Mikaya, Mass Spectrometry of Organic Compounds [in Russian], Khimiya, Moscow (1986), p. 139.

    Google Scholar 

  14. Organic Syntheses, Coll. Vol. 4 (1963), p. 364.

  15. F. Ullmann, G. Engi, N. Wosnessensky, E. Kuhn, and E. Herre, Liebigs Ann. Chem, 366, 103 (1909).

    Google Scholar 

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Authors and Affiliations

  1. Institute of Problems of Chemical Physics, Russian Academy of Sciences, 142432, Chernogolovka, Moscow Region, Russia

    S. M. Sipyagin, V. S. Enshov & S. A. Kashtanov

  2. Department of Chemistry, The University of Alabama, Tuscaloosa, AL, 35487-0336, USA

    J. S. Thrasher

Authors
  1. S. M. Sipyagin
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  2. V. S. Enshov
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  3. S. A. Kashtanov
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  4. J. S. Thrasher
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Sipyagin, S.M., Enshov, V.S., Kashtanov, S.A. et al. 1-Chloro-2,6-dinitro-4-perfluoroalkylthiobenzenes in the Synthesis of Heterocycles. Chemistry of Heterocyclic Compounds 38, 1375–1381 (2002). https://doi.org/10.1023/A:1022138711847

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