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Russian Chemical Bulletin

, Volume 44, Issue 4, pp 631–634 | Cite as

Nucleophilic substitution of halogen in 4-halogenated derivatives of glutamic acid

1. Solvent effect
  • V. P. Krasnov
  • M. A. Koroleva
Physical Chemistry

Abstract

The reaction of nucleophilic substitution of bromine byp-anisidine in dimethyl (2S,4S)-and (2S,4R)-N-phthaloyl-4-bromoglutamates proceeds according to the SN2 mechanism. The relative reactivity of diastereomers in various solvents was studied.

Key words

glutamic acid diastereoselectivity nucleophilic substitution rate constant solvent effect 

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References

  1. 1.
    G. M. Coppola and H. F. Schuster,Asymmetric Synthesis. Construction of Chiral Molecules Using Amino Acids, Wiley Interscience Publ. J. Wiley and Sons, New York-Chichester, 1987, 223.Google Scholar
  2. 2.
    Studies in Natural Products Chemistry. Stereoselective Synthesis (Part A), Ed. Atta-ur-Rahman, Elsevier, New York, 1988,1, 331.Google Scholar
  3. 3.
    J. E. Baldwin, T. Miranda, M. Moloney, and T. Hokelek,Tetrahedron, 1989,45, 7459.Google Scholar
  4. 4.
    Y. Izumi and A. Tai,Stereo-Differentiating Reactions. The Nature of Asymmetric Reactions, Kodansha Ltd., Tokyo, Academic Press, New York-San Francisco, 1977.Google Scholar
  5. 5.
    I. A. Nizova, V. P. Krasnov, O. V. Korotovskikh, and L. V. Alekseeva,Izv. Akad. Nauk SSSR, Ser. Khim., 1989, 2781 [Bull. Acad. Sci. USSR, Div. Chem. Sci, 1989,39, 2545 (Engl. Transl.)].Google Scholar
  6. 6.
    I. A. Nizova, V. P. Krasnov, T. A. Sinitsina, and N. V. Avdyukova,Izv. Akad. Nauk, Ser. Khim., 1993, 2087 [Russ. Chem. Bull., 1993,42, 2001 (Engl. Transl.)].Google Scholar
  7. 7.
    G. G. Vatulina, T. N. Tuzhilkova, T. V. Matveeva, V. P. Krasnov, N. L. Burde, and L. V. Alekseeva,Khim. Farm. Zhurn. [Chem. Pharm. J.], 1986,20, 1078 (in Russian).Google Scholar
  8. 8.
    C. Ducrocq, A. Righini-Tapie, R. Azerad, J. F. Green, P. A. Friedman, J.-P. Beaucourt, and B. Rousseau,J. Chem. Soc., Perkin Trans, 1, 1986, 1323.Google Scholar
  9. 9.
    V. P. Krasnov, I. M. Bukrina, E. A. Zhdanova, M. I. Kodess, and M. A. Korolyova,Synthesis, 1994, No 7.Google Scholar
  10. 10.
    C. K. Ingold,Structure and Mechanism in Organic Chemistry, Cornell Univ. Press, Ithaca and London, 1969.Google Scholar
  11. 11.
    A. R. Katritzky and B. E. Brycki,J. Phys. Org. Chem., 1988,1, 1.Google Scholar
  12. 12.
    N. S. Isaacs,Physical Organic Chemistry, Longman Sci. and Tech., Belfast, 1987, 315.Google Scholar
  13. 13.
    B. Bandy,Metody optimizatsii [Optimization Procedures], Radio i Svyaz', Moscow, 1988, 37 pp. (in Russian).Google Scholar
  14. 14.
    L. P. Hammet,Physical Organic Chemistry, McGraw Hill Book Company, New York, 1970.Google Scholar
  15. 15.
    V. Gutmann,Coord. Chem. Rev., 1976,18, 225.Google Scholar
  16. 16.
    W. R. Fawcett and T. M. Krygowski,Can. J. Chem., 1976,54, 3283.Google Scholar
  17. 17.
    W. R. Fawcett and T. M. Krygowski,J. Am. Chem. Soc., 1975,97, 2143.Google Scholar
  18. 18.
    V. Gutmann,Electrochem. Acta, 1976,21, 661.Google Scholar

Copyright information

© Plenum Publishing Corporation 1995

Authors and Affiliations

  • V. P. Krasnov
    • 1
  • M. A. Koroleva
    • 1
  1. 1.Institute of Organic SynthesisUral Branch of the Russian Academy of SciencesEkaterinburgRussian Federation

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