Skip to main content
Log in

Synthesis of stereoisomeric organomercury compounds via organolithium compounds

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

Summary

  1. 1.

    By treatment of the geometric isomers of 1,2-diphenylvinyllithium with mercuric chloride, the stereoisomeric bis(1,2-diphenylvinyl)mercurys have been prepared.

  2. 2.

    By the disymmetrization of the stereoisomeric bis(1,2-diphenylvinyl)mercurys, the stereoisomeric 1,2-diphenylvinyl mercury chlorides have been prepared.

  3. 3.

    An investigation has been made of the symmetrization of the stereoisomeric 1,2-diphenylvinylmercury chlorides with formation of the original bis(1,2-diphenylvinyl)mercurys.

  4. 4.

    A study has been made of the conditions required for the isomerization of cis-1,2-diphenylvinyllithium and of cis-bis(1,2-diphenylvinyl)mercury into the corresponding trans isomers.

  5. 5.

    It has been shown that the investigated exchange reactions occurring at the olefin carbon responsible for geometric isomerism are stereochemically pure and occur without change in the original configuration.

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.

Similar content being viewed by others

Literature Cited

  1. A. N. Nesmeyanov, A. E. Borisov, and A. N. Guskova, Bull. Acad. Sci. USSR, Div. Chem. Sci., 1945, 639.

  2. A. N. Nesmeyanov, A. E. Borisov, and A. N. Abramova, Bull. Acad. Sci. USSR, Div. Chem. Sci., 1946, 647.

  3. R. Kh. Freidlina, A. K. Kochetkov, and A. N. Nesmeyanov, Bull. Acad. Sci. USSR, Div. Chem. Sci., 1948, 445.

  4. A. N. Nesmeyanov, A. E. Borisov, and A. N. Abramova, Bull. Acad. Sci. USSR, Div. Chem. Sci., 1949, 570.

  5. A. N. Nesmeyanov, A. E. Borisov, and R. I. Shepeleva, Bull. Acad. Sci. USSR, Div. Chem. Sci., 1949, 582.

  6. A. E. Borisov, Bull. Acad. Sci. USSR, Div. Chem. Sci., 1951, 402.

  7. A. N. Nesmeyanov and A. E. Borisov, Proc. Acad. Sci. USSR, 60, 67 (1948).

    Google Scholar 

  8. C. F. Koelsch, J. Am. Chem. Soc., 54, 2045, 2487 (1932).

    Google Scholar 

  9. H. Rupe, H. Proske, Ber. 43, 1231 (1910).

    Google Scholar 

  10. H. Gilman, W. Langham, F. W. Moore, J. Am. Chem. Soc., 62, 2327 (1940).

    Google Scholar 

  11. E. A. Braude, J. A. Coles, J. Chem. Soc., 1951, 2078, 1952, 1425.

  12. D. Y. Curtin, E. E. Harris, J. Am. Chem. Soc., 73, 4519 (1951).

    Google Scholar 

  13. G. F. Wright, J. org. Chem. 1, 457 (1936).

    Google Scholar 

  14. A. N. Nesmeyanov and T A. Kudryavtseva, Sci. Mem. Moscow State Univ., 151, No. 8, 57 (1951).

    Google Scholar 

  15. J. Wislicenus, F. Seeler, Ber. 28, 2700 (1895).

    Google Scholar 

  16. F. Straus, Ann. 342, 262 (1905).

    Google Scholar 

  17. J. Errera, V. Henri, Comptes rend., 181, 548, (1925)

    Google Scholar 

  18. A. Smakula, A. Wassermann, Z. phys. Chem., 155, 353 (1931).

    Google Scholar 

  19. U. V. Solmssen, J. Am. Chem. Soc. 65, 2373 (1943).

    Google Scholar 

  20. J. F. Codington, E. Mosettig, J. org. chem. 17, 1035 (1952).

    Google Scholar 

  21. G. A. R. Kon, R. G. W. Spickett, J. Chem. Soc., 1949, 2724.

  22. B. Arends, Ber. 64, 1936 (1931).

    Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Rights and permissions

Reprints and permissions

About this article

Cite this article

Nesmeyanov, A.N., Borisov, A.E. & Volkenau, N.A. Synthesis of stereoisomeric organomercury compounds via organolithium compounds. Russ Chem Bull 3, 865–872 (1954). https://doi.org/10.1007/BF01168169

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF01168169

Keywords

Navigation