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Reaction of hexafluorobutadiene with sulfur trioxide

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

Conclusions

  1. 1.

    Hexafluorobutadiene and sulfur trioxide do not form the Diels-Alder adducts. The primary reaction product is 4-(trifluorovinyl)-3,3,4-trifluoro-1-oxa-2-thiacyclobutane 2,2-dioxide (a 3-sultone).

  2. 2.

    When stored or heated the β-sultone undergoes retrocycloaddition and isomerization to a 6-sultone and a linear 1,4-copolymer of hexafluorobutadiene and SO3 (1:1).

  3. 3.

    The oxidation-reduction reaction of the β-sultone with SO3 forms 4-(trifluorovinyl)-4,5,5-trifluoro-1,3-dioxa-2-thiacyclopentane 2,2-dioxide (a β-sulfate), the corresponding polyperfluoropyrosulfate, and SO2.

  4. 4.

    The β-sulfate is thermally isomerized to δ -sulfate (4,4,5,6,7,7-hexafluoro-1,3-dioxa-2-thia-5-cycloheptene 2,2-dioxide).

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Literature cited

  1. C. R. Brundle and M. B. Robin, J. Am. Chem. Soc.,92, 5550 (1970).

    Google Scholar 

  2. R. E. Banks, A. C. Harrison, R. N. Haszeldine, and K. G. Orrell, J. Chem. Soc. C,1967, 1608.

    Google Scholar 

  3. V. A. Ginzburg, A. N. Medvedev, S. S. Dubov, P. O. Gitel', V. V. Smolyanitskaya, and G. E. Nikolaenko, Zh. Obshch. Khim.,39, 282 (1969).

    Google Scholar 

  4. R. E. Banks, M. G. Barlow, and R. N. Haszeldine, J. Chem. Soc.,1965, 6149.

  5. N. B. Kaz'mina, I. L. Knunyants, E. I. Mysov, and G. M. Kuz'yants, Izv. Akad. Nauk SSSR Ser. Khim.,1977, 163.

  6. I. L. Knunyants (Knunjanz) and G. A. Sokol'skii (Sokolski), Angew. Chem.,84, 623 (1972).

    Google Scholar 

  7. B. E. Smart, J. Org. Chem.,41, 2353 (1976).

    Google Scholar 

  8. C. G. Krespan, B. E. Smart, and E. G. Howard, J. Am. Chem. Soc.,99, 1214, 1218 (1977).

    Google Scholar 

  9. G. A. Sokol'skii, M. A. Belaventsev, and I. L. Knunyants, Izv. Akad. Nauk SSSR, Ser. Khim.,1968, 1076.

  10. I. L. Knunyants, V. V. Shokina, and E. I. Mysov, Izv. Akad. Nauk SSSR, Ser. Khim.,1973, 2725.

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Authors and Affiliations

  1. Institute of Heteroorganic Compounds, Academy of Sciences of the USSR, Moscow

    N. B. Kaz'mina, I. L. Knunyants, G. M. Kuz'yants, E. I. Mysov & É. P. Lur'e

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  1. N. B. Kaz'mina
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  2. I. L. Knunyants
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  3. G. M. Kuz'yants
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  4. E. I. Mysov
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  5. É. P. Lur'e
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Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 1, pp. 118–126, January, 1979.

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Kaz'mina, N.B., Knunyants, I.L., Kuz'yants, G.M. et al. Reaction of hexafluorobutadiene with sulfur trioxide. Russ Chem Bull 28, 106–114 (1979). https://doi.org/10.1007/BF00925407

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  • DOI: https://doi.org/10.1007/BF00925407

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