Skip to main content
Log in

Reformatsky-type addition of esters of α-halogeno carboxylic acids to aldehydes and ketones in the presence of Fe(CO)5

  • Organic Chemistry
  • Published:
Russian Chemical Bulletin Aims and scope

Abstract

Reformatsky-type addition of esters of α-halogeno carboxylic acids to aldehydes and ketones in the presence of Fe(CO)5 and an activating agent (CBrCl3 or I2) afforded the corresponding esters of β-hydroxy acids in good yields. Possible reaction mechanisms are discussed.

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

References

  1. R. L. Shriner,Org. React., 1942,1; 1; A. Furstner,Synthesis, 1989, 571; H. Kagoshima, Y. Hashimoto, D. Oguro, and K. Saigo,J. Org. Chem., 1998,63, 691.

    Google Scholar 

  2. L. Wessjohann and H. Wild,Synlett, 1997,6, 731; F. Orsini,J. Org. Chem., 1997,62 1159; P. Girard, J. L. Namy, and H. B. Kagan,J. Am. Chem. Soc., 1980,102, 2693; C.-J. Li,Tetrahedron, 1996,52, 5643; C.-J. Li,Chem. Rev., 1993,93, 2023; G. A. Molander and C. R. Harris,Chem. Rev., 1996,96, 307.

    Google Scholar 

  3. A. B. Terentiev, T. T. Vasilieva, N. A. Kuz'mina, E. I. Mysov, N. Yu. Kuznetsov, and Yu. N. Belokon',J. Chem. Research (M), 1998, 1281.

  4. V. G. Syrkin,Karbonily metallov [Metal Carbonyls], Khimiya, Moscow, 1983, 30 (in Russian).

    Google Scholar 

  5. A. M. Bond, P. A. Dawson, B. M. Peake, B. H. Robinson, and J. Simpson,Inorg. Chem., 1977,16, 2199.

    Article  CAS  Google Scholar 

  6. J. Canceill, J.-J. Basselier, and J. Jacques,Bull. Soc. Chim. Fr., 1967, 1024.

  7. R. Kh. Freidlina, F. K. Velichko, S. S. Zlotskii, D. L. Rakhmankulov, and A. B. Terent'ev,Radikal'naya telomerizatsiya [Radical Telomerization], Khimiya, Moscow, 1988 (in Russian).

    Google Scholar 

  8. H. B. Kagan, J. L. Namy, and P. Girard,Tetrahedron, 1981,37, Suppl. 1, 175.

    Article  Google Scholar 

  9. D. P. Curran, Th. L. Fevig, C. P. Jasperse, and M. J. Totleben,Synlett, 1992, 943.

  10. P. K. Baker, N.G. Connely, B. M. R. Jones, J. P. Maher, and K. R. Somers,J. Chem. Soc., Dalton Trans., 1980, 579.

  11. C. P. Jasperse, Th. L. Fevig, and D. P. Curran,Chem. Rev., 1991,91, 1237.

    Article  CAS  Google Scholar 

  12. R. T. Jonas and D. P. Stack,J. Am. Chem. Soc., 1997,119, 8566.

    Article  CAS  Google Scholar 

  13. R. G. Hofstraat, H. W. Scheeren, and R. G. F. Nivard,J. Chem. Soc., Perkin Trans. 1, 1985, 561.

    Article  Google Scholar 

  14. J. B. Woofen and Y. Houminer,J. Org. Chem., 1982,47, 5102.

    Article  Google Scholar 

  15. A. Conan, S. Sibille, and J. Perichon,J. Org. Chem., 1991,56, 2018.

    Article  CAS  Google Scholar 

  16. K. Takai, Y. Hotta, K. Oshima, and H. Nozaki,Bull. Chem. Soc. Jpn., 1980,53, 1698.

    Article  CAS  Google Scholar 

  17. A. B. Terent'ev, T. T. Vasil'eva, N. A. Kuz'mina, N. S. Ikonnikov, S. A. Orlova, E.I. Mysov, and Yu. N. Belokon',Izv. Akad. Nauk, Ser. Khim., 1997, 2210 [Russ. Chem. Bull., 1997,46, 2096 (Engl. Transl.)].

    Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Additional information

Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 6, pp. 1132–1138, June, 1999.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Terent'ev, A.B., Vasil'eva, T.T., Kuz'mina, N.A. et al. Reformatsky-type addition of esters of α-halogeno carboxylic acids to aldehydes and ketones in the presence of Fe(CO)5 . Russ Chem Bull 48, 1121–1127 (1999). https://doi.org/10.1007/BF02496013

Download citation

  • Received:

  • Revised:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF02496013

Key words

Navigation