Two-step phosphorus-mediated substitution of hydroxy groups in selected primary alcohols for fluorinated alkyl or aryl substituents: the molecular structure of 1,1-bis(fluorosulfonyl)-1-fluoro-2-phenylethane

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Alexander Kolomeitsev, Alexander Shtarev, Kyrill Chabanenko, Tatjana Savina, Yurii Yagupolskii, Alexander Shtarev, Kyrill Chabanenko, Yurii Yagupolskii, Michaela Görg, Jan Przyborowski, Enno Lork and Gerd-Volker Röschenthaler


Abstract

In an Arbuzov type reaction, amido phosphites (Et2N)2- PORand a broad range of halofluoro organic halides (X = Cl, Br) formed the corresponding alkylated derivatives R1–R2 [R1 = Bn, R2 = C(SO2F)3, CCl2F, CCl2CF3, CBr2F, C(CF3)3, C6F5; R1 = Et, CH2CF3, Me, R2 = CCl2CF3], whereas with FC(SO2F)3 and loss of SO2, BnCF(SO2F)2 was obtained, as shown by X-ray crystallography.


References

  1. J. T. Welch and S. Eswarakrishnan, Fluorine in Bioorganic Chemistry, Wiley, New York, 1991 Search PubMed; Organofluorine Compounds in Medicinal Chemistry and Biomedical Applications, ed. R. Filler, Y. Kobayashi and L. M. Yagupolskii, Elsevier, Amsterdam, 1993 Search PubMed.
  2. G. K. Surya Prakash and A. K. Yudin, Chem. Rev., 1997, 97, 757 CrossRef CAS; M. Yoshida, D. Suzuki and M. Iyoda, J. Chem. Soc., Perkin Trans. 1, 1997, 643 RSC; F. Hong and C.-M. Hu, Chem. Commun., 1996, 57 RSC.
  3. I. Ruppert, K. K. Schlich and W. Volbach, Tetrahedron Lett., 1984, 25, 2195 CrossRef CAS.
  4. A. N. Chernega, A. A. Kolomeitsev, Yu. L. Yagupolskii, A. Gentzsch and G.-V. Röschenthaler, J. Fluorine Chem., 1995, 70, 271 CrossRef CAS.
  5. A. A. Kolomeitsev, K. Y. Chabanenko, G.-V. Röschenthaler and Yu. L. Yagupolskii, Synthesis, 1994, 145 CrossRef CAS.
  6. V. S. Abramov and N. A. Il'ina, Zh. Obshch. Khim., 1971, 41, 100 CAS.
  7. J. H. Hargis and W. D. Alley, J. Am. Chem. Soc., 1974, 96, 5927 CrossRef CAS.
  8. A. P. Marchenko, G. N. Kojdan, G. O. Baram, A. N. Chernega and A. N. Pinchuk, Zh. Obshch. Khim., 1994, 64, 821.
  9. G. Klöter, H. Pritzkow and K. Seppelt, Angew. Chem., 1980, 92, 954.
  10. J. Y. Nedelec, H. Ait-Haddou-Mouloud, J. C. Folest and J. Perichon, Tetrahedron Lett., 1988, 29, 1699 CrossRef CAS.
  11. W. Dmowski and R. Kolinski, Rocz. Chem., 1973, 47, 1211 Search PubMed.
  12. X.-Z. Qin, Q.-C. Meng and F. Williams, J. Am. Chem. Soc., 1987, 109, 6778 CrossRef CAS.
  13. R. N. Haszeldine and F. Nyman, J. Chem. Soc., 1959, 387 RSC.
  14. W. B. Farnham and J. C. Calabrese, J. Am. Chem. Soc., 1986, 108, 2449 CrossRef CAS.
  15. Synthesis of Fluoroorganic Compounds, ed. I. L. Knunyants and G. G. Yakobson, Springer, Berlin, 1985, p. 129 Search PubMed.
  16. M. Görg, A. A. Kolomeitsev and G.-V. Röschenthaler, Phosphorus Sulfur Silicon Relat Elem., in the press Search PubMed.
  17. A. A. Kolomeitsev and G.-V. Röschenthaler, unpublished results.
  18. Yu. L. Yagupolskii, T. I. Savina, N. V. Pavlenko, A. A. Pankov and S. V. Pazenok, Zh. Obshch. Khim., 1991, 61, 1512 CAS.
  19. N. S. Zefirov and D. I. Makhon'kov, Chem. Rev., 1982, 82, 615 CrossRef CAS.
  20. A. K. Bhattacharya and G. Thyargarayan, Chem. Rev., 1981, 81, 415 CrossRef CAS; J. Michalski, A. Skowronska and R. Bodalski, in Phosphorus-31 Spectroscopy in Stereo-chemical Analysis, ed. J. G. Verkade and L. D. Quin, VCH, Deerfield Beach, 1987, p. 255 Search PubMed.
  21. International Tabels for Crystallography, Vol. C, ed. A. J. C. Wilson, Kluwer, Dordrecht, 1995, p. 691 Search PubMed.
  22. M. Van Der Puy, J. Fluorine Chem., 1997, 81, 187 CrossRef; J. E. Bunch and C. L. Bumgardner, ibid, 1987, 36, 313 Search PubMed; W. Dmowski, ibid, 1985, 29, 287 Search PubMed; M. Makosza and H. Plienkiewicz, ibid, 1984, 24, 387 Search PubMed; Y. Kobayashi, T. Yamashita, K. Takahashi, H. Kuroda and I. Kumadaki, Tetrahedron Lett., 1982, 23, 343 CrossRef CAS; H. F. Koch, W. Tumas and R. Knoll, J. Am. Chem. Soc., 1981, 103, 5323; L. M. Yagupolskii and Y. A. Filyakov, Zh. Obshch. Khim., 1960, 30, 1291 CAS.
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