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Unusual cleavage of adducts of trialkyl phosphites with perfluoromethacrylic acid derivatives

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

Conclusions

  1. 1.

    Perfluoromethaerylic acid derivatives when reacted with trialkyl phosphites give stable adducts that contain a pentacoordinated phosphorus atom, and specifically are substitutedα-fluorovinyltrialkoxy-fluorophosphoranes.

  2. 2.

    The phosphoranes obtained from perfluoromethacrylic acid esters and trialkyl phosphites are cleaved when heated, in which connection the products of the Arbuzov reaction are not formed, but instead alkyl difluorophosphites and the esters ofα-trifluoromethyl-β,β-dialkoxyacrylic acids.

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Literature cited

  1. U. Utebaev, E. M. Rokhlin E. P. Lur'e, and I. L. Knunyants, Izv. Akad. Nauk SSSR, Ser. Khim.,1975, 1463.

  2. I. L. Knunyants, V. V. Tyuleneva, E. Ya. Perova, and R. N. Sterlin, Izv. Akad. Nauk SSSR, Ser. Khim.,1964, 1797.

  3. U. Utebaev, E. M. Rokhlin, E. P. Lur'e, and I. L. Knunyants, Izv. Akad. Nauk SSSR, Ser. Khim.,1976, 142.

  4. E. G. Abduganiev, É. A. Avetisyan, E. M. Rokhlin, and I. L. Knunyants, Izv. Akad. Nauk SSSR, Ser. Khim.,1974, 392.

  5. I. L. Knunyants, Yu. A. Cheburkov, M. D. Bargamova, É. I. Fedin, and P. V. Petrovskii, Izv. Akad. Nauk SSSR, Ser. Khim.,1966, 1031.

  6. T. Ueda, K. Inukai, and H. Muramatsu, Bull. Chem. Soc. Japan,42, 1684 (1969).

    Google Scholar 

  7. R. Hudson, Structure and Reaction Mechanism of Organophosphorus Compounds [Russian translation], Mir (1967), p. 253; T. Kh. Gazizov, Yu. Ya. Efremov, R. Z. Musin, A. P. Pashinkin, V. A. Kharlamov, and A. N. Pudovik, Zh. Obshch. Khim.,44, 1859 (1974).

  8. I. L. Knunyants, É. G. Bykhovskaya, V. N. Volkovitskii, V. F. Plotnikov, I. V. Galakhov, and L. I. Ragulin, Zh. Vses. Khim. Obshchestva D. I. Mendeleeva,17, 598 (1972).

    Google Scholar 

  9. A. N. Pudovik, Yu. I. Sudarev, A. P. Pashinkin, V. I. Kovalenko, A. M. Kibardin, and T. Kh. Gazizov, Dokl. Akad. Nauk SSSR,218, 359 (1974).

    Google Scholar 

  10. M. I. Kabachnik and P. A. Rossiiskaya, Izv. Akad. Nauk SSSR, Otd. Khim. Nauk,1945, 364.

  11. K. Sasse, Methoden der organischen Chemie (Houben-Weyl), Vol. 12/1, G. Thieme, Stuttgart (1963), p. 453.

    Google Scholar 

  12. N. N. Sazonova, Dissertation [in Russian], Kazan (1960); I. S. Akhmetzhanov, Zh. Obshch. Khim.,44, 1452 (1974).

  13. É. E. Nifant'ev, Chemistry of Organophosphorus Compounds [in Russian], Izd. Moskov. Univ. (1971), p. 25.

  14. F. Seel, R. Budenz, and K. Gruner, Liebigs Ann. Chem.,684, 1 (1965).

    Google Scholar 

  15. K. Sasse, Methoden der organischen Chemie (Houben-Weyl), Vol. 12/2, G. Thieme, Stuttgart (1964), pp. 18, 50.

    Google Scholar 

  16. D. Hellwinkel, Organic Phosphorus Compounds, G. M. Kosolapoff and L. Maier (editors), Vol. 3, J. Wiley, New York (1972), p. 187; W. Gerard and H. R. Hudson, Ibid., Vol. 5, pp. 38, 58 (1973); J. Gloede, J. Prakt. Chem.,316, 703 (1974).

    Google Scholar 

  17. A. F. Divinskii, M. I. Kabachnik, and V. V. Sidorenko, Dokl. Akad. Nauk SSSR,60, 999 (1948); E. A. Krasil'nikova, A. M. Potapov, and A. I. Razumov, Zh. Obshch. Khim.,38, 609 (1968).

    Google Scholar 

  18. D. H. Brown, K. D. Crosbie, G. W. Fraser, and D. W. Sharp, J. Chem. Soc., A 1969, 872.

    Google Scholar 

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See [1] for preliminary communication.

Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 4, pp. 875–882, April, 1976.

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Knunyants, I.L., Utebaev, U., Rokhlin, E.M. et al. Unusual cleavage of adducts of trialkyl phosphites with perfluoromethacrylic acid derivatives. Russ Chem Bull 25, 853–860 (1976). https://doi.org/10.1007/BF00922396

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  • DOI: https://doi.org/10.1007/BF00922396

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