Skip to main content
Log in

PdCl2-catalyzed hydrogenolysis of a C-O bond in monoaryl sulfates by sodium phosphinate in an aqueous alkaline medium

  • Brief Communications
  • Published:
Russian Chemical Bulletin Aims and scope

Abstract

The hydrogenolysis of the C-O bond in monoaryl sulfates by the action of an excess of NaH2PO2 in the presence of catalytic amounts of PdCl2 and KOH is studied. The reaction proceeds chemoselectively with complete ester conversion to the corresponding arenes.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

References

  1. J. I. DeGraw, J. C. Christinsen, V. H. Brown, and M. J. Cory,J. Heterocycl. Chem., 1974,11, 363.

    Google Scholar 

  2. S. Sakai, A. Kubo, T. Hamamoto, M. Wakabayashi, K. Takahashi, J. Haginiva, and Y. Ohtani,Tetrahedron Lett., 1969,19, 1489.

    Google Scholar 

  3. C. F. Barfknecht, R. V. Smith, and V. D. Reif,Can. J. Chem., 1970,48, 2138.

    Google Scholar 

  4. H. C. Beyerman, E. Buurman, T. S. Lie, and L. Maat,Rec'. Trav. Chim. Pays-Bas, 1976,95, 43.

    Google Scholar 

  5. L. R. Subramanian, A. G. Martinez, A. H. Fernandez, and R. M. Alvarez,Synthesis, 1984, 143, N574-016, 481.

    Google Scholar 

  6. S. Cacci, P. Gp Giattini, E. Morrera, and G. Ortar,Tetrahedron Lett., 1986,27, 5541.

    Google Scholar 

  7. Q. Y. Chen and Y. B. He,Synthesis, 1988, 896.

  8. B. J. Hassey, R. A. W. Johnstone, and I. D. Entwistle,Tetrahedron, 1982,38, 3775.

    Google Scholar 

  9. G. A. Peterson, F. A. Kunng, J. S. McCallum, and W. D. Wulf,Tetrahedron Lett., 1987,28, 1380.

    Google Scholar 

  10. E. Vowinkel and H. J. Baese,Chem. Ber., 1974,107, 1213.

    Google Scholar 

  11. E. Vowinkel and C. Wolff,Chem. Ber., 1974,107, 907.

    Google Scholar 

  12. J. D. Weaver, E. J. Eisenbraun, and L. E. Harris,Chem. Ind. (London), 1973, 187.

  13. W. J. Musliner and J. W. Gates,J. Am. Chem. Soc., 1966,88, 4271.

    Google Scholar 

  14. T. Shono, Y. Matsumoto, K. Tsubata, and Y. Sugihara,J. Org. Chem., 1979,44, 4508.

    Google Scholar 

  15. W. Lonsky, H. Traitler, and K. Kratzl,J. Chem. Soc., Perkin Trans., 1, 1975, 169.

    Google Scholar 

  16. D. V. Davydov and I. P. Beletskaya,Metalloorg. Khim., 1983,6, 11. [J. Organomet. Chem. USSR, 1983,6 (Erigl. Transl.)].

    Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Additional information

Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 3, pp. 605–606, March, 1993.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Davydov, D.V., Beletskaya, I.P. PdCl2-catalyzed hydrogenolysis of a C-O bond in monoaryl sulfates by sodium phosphinate in an aqueous alkaline medium. Russ Chem Bull 42, 573–575 (1993). https://doi.org/10.1007/BF00698458

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF00698458

Key words

Navigation