Springer Nature is making SARS-CoV-2 and COVID-19 research free. View research | View latest news | Sign up for updates

Reactions of some unsaturated compounds with hydrogenation products of ethylmagnesium bromide

  • 20 Accesses

Conclusions

  1. 1.

    Ethynyltri-n-butyltin reacts with the hydrogenation product of C2H5MgBr in THF, and in benzene containing traces of ether, with a cleavage of the C-Sn bond and the formation of acetylene, tri-n-butyltin hydride, vinyltri-n-butyltin, and a mixture of the cis- and trans-isomers of l,2-bis(tri-n-butylstannyl)-ethylene). In benzene this reaction proceeds with the liberation of acetylene and the formation of one of the l,2-bis(tri-n-butylstannyl)ethylene isomers.

  2. 2.

    Phenylpropiolic acid and styrene are formed when phenylacetylene is heated with the hydrogenation product of C2H5MgBr in THF and subsequent carbonation.

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

Literature cited

  1. 1.

    T. N. Dymova and N. G. Eliseeva, Zh. Neorgan. Khim.,8, 1574 (1963).

  2. 2.

    E. C. Ashby, R. A. Kovar, and K. Kawakami, Inorg. Chem.,9, 317 (1970).

  3. 3.

    W. E. Becker and E. C. Ashby, J. Org. Chem.,29, 954 (1964).

  4. 4.

    H. E. Podall and W. E. Foster, J. Org. Chem.,23, 1848 (1958).

  5. 5.

    E. Field and M. Feller, US Patent 2,731,452 (January 17, 1956); C. A.,50, 6092 (1956).

  6. 6.

    E. Field and M. Feller, US Patent 2,773,053 (December 4, 1956); C. A.,51, 4051 (1957).

  7. 7.

    K. Ziegler, German Patent 889,229 (September 7, 1953); C. A.,52, 12457 (1958).

  8. 8.

    L. H. Slaugh, J. Org. Chem.,32, 108 (1967).

  9. 9.

    H. D. Ledbetter, US Patent 3,478,008 (November 11, 1969); C.A.,72, 22134 (1970).

  10. 10.

    M. Marek and L. O. Toman, German Patent 2,140,448 (February 17, 1972); C.A.,76, 154480 (1972).

  11. 11.

    A. N. Nesmeyanov and A. E. Borisov, Dokl. Akad. Nauk SSSR,174, 96 (1967).

  12. 12.

    L. Ilosvay, Chem. Ber.,32, 2698 (1899).

  13. 13.

    A. N. Nesmeyanov and A. E. Borisov, Izv. Akad. Nauk SSSR, Ser. Khim., 226 (1967).

  14. 14.

    F. Barisch, J. Prakt. Chem., [2]20, 181 (1879).

Download references

Author information

Additional information

Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 11, pp. 2557–2558, November, 1974.

The author expresses his deep gratitude to P. V. Petrovskii and I. D. Rubin for taking and deciphering the spectra.

Rights and permissions

Reprints and Permissions

About this article

Cite this article

Savel'eva, I.S. Reactions of some unsaturated compounds with hydrogenation products of ethylmagnesium bromide. Russ Chem Bull 23, 2464–2465 (1974). https://doi.org/10.1007/BF00922132

Download citation

Keywords

  • Hydrogenation
  • Ethylene
  • Benzene
  • Bromide
  • Hydride