Russian Chemical Bulletin

, Volume 44, Issue 4, pp 635–638 | Cite as

Nucleophilic substitution of halogen in 4-halo genated derivatives of glutamic acid

2. Structural effects of arylamine as nucleophile
  • V. P. Krasnov
  • M. A. Koroleva
  • N. G. Evstigneeva
  • I. A. Nizova
Physical Chemistry

Abstract

Kinetics of nucleophilic substitution of halogen in diastereomeric dimethyl 4-bromo- and 4-iodoglutamates withortho-, meta-, andpara-substituted anilines was studied by HPLC. Thethreo-diastereomers of the halogenated derivatives react 3–5 times faster than theerythro ones. The structure of the transition state is discussed.

Key words

glutamic acid diastereoselectivity nucleophilic substitution rate constant arylamine 

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Copyright information

© Plenum Publishing Corporation 1995

Authors and Affiliations

  • V. P. Krasnov
    • 1
  • M. A. Koroleva
    • 1
  • N. G. Evstigneeva
    • 1
  • I. A. Nizova
    • 1
  1. 1.Institute of Organic SynthesisUral Branch of the Russian Academy of SciencesEkaterinburgRussian Federation

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